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Rodriguez, Diego F. ; Duran-Osorio, Francisca ; Duarte, Yorley , et al. Pharmaceutics,2022,14(1),33. DOI: 10.3390/pharmaceutics14010033 PubMed ID: 35056929
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Abstract: Green chemistry implementation has led to promising results in waste reduction in the pharmaceutical industry. However, the early sustainable development of pharmaceutically active compounds and ingredients remains a considerable challenge. Herein, we wish to report a green synthesis of new pharmaceutically active peptide triazoles as potent factor Xa inhibitors, an important drug target associated with the treatment of diverse cardiovascular diseases. The new inhibitors were synthesized in three steps, featuring cycloaddition reactions (high atom economy), microwave-assisted organic synthesis (energy efficiency), and copper nanoparticle catalysis, thus featuring Earth-abundant metals. The molecules obtained showed FXa inhibition, with IC50-values as low as 17.2 μM and no associated cytotoxicity in HEK293 and HeLa cells. These results showcase the environmental potential and chemical implications of the applied methodologies for the development of new molecules with pharmacological potential.
Keywords: DOACs ; FXa inhibitors ; Ullmann-Goldberg reaction ; click chemistry ; drug discovery ; green chemistry ; microwave synthesis
Purchased from AmBeed: 20196-21-8 ; 109-11-5 ; 675-20-7 ; 766-97-2
CAS No. : | 109-11-5 | MDL No. : | MFCD00631009 |
Formula : | C4H7NO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | VSEAAEQOQBMPQF-UHFFFAOYSA-N |
M.W : | 101.10 | Pubchem ID : | 66953 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94.21% | With dmap; triethylamine; In dichloromethane; at 20℃; for 16h; | To a solution of <strong>[109-11-5]morpholin-3-one</strong> (6.4 g, 63.30 mmol, 1.0 eq) in DCM (100 mL) at 20 C was added TEA (19.22 g, 189.90 mmol, 26.4 mL, 3.0 eq), DMAP (1.55 g, 12.66 mmol, 0.2 eq) and then Boc2O (27.63 g, 126.60 mmol, 29.1 mL, 2.0 eq), and the resulting mixture was stirred at 20 C for 16 h. The reaction mixture was concentrated to remove the solvent and the residue was diluted with water (200 mL) and extracted with EA (100 mL *3). The combined organic layers were washed with water (50 mL *3) and then brine (100 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by flash silica gel chromatography to give tert-butyl 3-oxomorpholine-4- carboxylate (12.0 g, 59.64 mmol, 94.21% yield) as yellow oil. 1H NMR (400 MHz, CDCI3) δ 4.23 (s, 2H), 3.93 - 3.87 (m, 2H), 3.79 - 3.72 (m, 2H), 1.55 (s, 9H). di-tert-butyl 3-oxomorpholine-2,4-dicarboxylate |
76% | With dmap; In tetrahydrofuran; at 20℃; for 24h; | Step 1: 7?ri-butyl 3-oxomorpholine- -carboxylate [00197] Morpholin-3-one (35g, 346.2 mmol) was slurried in dry THF (350ml). Tert- butoxycarbonyl tert- butyl carbonate (105.8g, 11 1.4 mmol) was added, followed by DMAP (4.2g, 34.6 mmol). The mixture began to degass rapidly over 30 minutes. The resulting orange solution was stirred at ambient temperature for 24hrs. The mixture was then cooled in an ice bath and imidazole (23.57g, 346.2 mmol) was added. After stirring for 30 minutes ethyl acetate (500ml) was added. The organic phase was separated and washed with 1% (v/v) HC1 (500ml), then sat NaHC03 (500ml), then brine (200ml), dried (MgS04), filtered and concentrated. The crude was purified through a plug of silica gel, eluting with ethyl acetate. The filtrate was evaporated to give an oil. 40/60 pet ether (200ml) was added slowly with stirring to generate a white solid. The mixture was aged for 30 minutes, cooled briefly in an ice bath and filtered, washing with 40/60 pet ether. Tert-butyl 3-oxomorpholine-4- carboxylate was obtained as a white solid which was dried under vacuum (52.7g, 76%); lH- NMR (CDCI3) 1.47 (9H, s), 3.68 (2H, m), 3.82 (2H, m), 4.15 (2H, s); MS ES(+) 145.8 (M+ - tBu). |
66% | With dmap; In tetrahydrofuran; at 20℃;Inert atmosphere; | Morpholmn-3-one (8.00 g, 79.2 mmcl) was dissolved in dry THE (100 mL), and then (Boc)20 (25.9 g, 0.119 mol) and DMAP (966 mg, 7.92 mmol) were added. The mixture was stirred at room temperature under N2 atmosphere overnight. Imidazole (5.39 g, 79.2 mmol) was added. After stirred for 30 mm EtOAc (150 mL) was added. The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to give oil whichwas solidified after standing. The solid was washed with PE (100 mL)to afford the desired compound (10.5 g, yield 66%) as a white solid.1H NMR (300 MHz, CDCI3): 64.20 (s, 2H), 3.88-3.85 (m, 2H), 3.74-3.70 (m, 2H), 1.51 (s, 9H).LC-MS (mobile phase: from 95% water and 5% CH3CN to 5% water and 95% CH3CN in 3.0mm, purity is >95%, Rt = 1.56 mm; MS Calcd.: 201; MS Found: 202 [M+H] 146 [M-56+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 8-quinolinol; potassium carbonate;copper(l) iodide; In dimethyl sulfoxide; at 130℃; | A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 prepared in Example 1 (33 mg, 0.074 mmol), <strong>[109-11-5]3-morpholinone</strong> prepared above (22 mg, 0.218 mmol), 8-hydroxyquinoline (7 mg, 0.048 mmol) and K2CO3 (30 mg, 0.217 mmol) in DMSO (0.5 mL) was degassed before being charged with CuI (14 mg, 0.073 mmol). The mixture in a sealed tube was heated at 130 C. overnight. The mixture was then purified by HPLC to give the title compound (3 mg). MS 417.0 and 419.0 (M+H, Cl pattern). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 95℃; for 16h; | 1.00 g (3.85 mmol) methyl 4-bromo-3-nitro-benzoate are dissolved in 6 ml dioxane with 389 mg (3.85 mmol) <strong>[109-11-5]morpholin-3-one</strong> under a nitrogen atmosphere and 36.6 mg (40 μmol) tris-(dibenzylideneacetone)-dipalladium(0), 67.1 mg (116 μmol) xantphos and 1.75 g (5.38 mmol) caesium carbonate are added. Under a nitrogen atmosphere and with stirring, the reaction mixture is heated to 95 C. for 16 hours. Then it is filtered, the solution is evaporated down i. vac. and evaporated with ether. The residue is further reacted without any more purification. Yield: 1.31 g (quantitative). C12H12N2O6 (280.24) Mass spectrum: (M+H)+=281 Rf value: 0.47 (Reversed phase 8; methanol/5% sodium chloride solution=6:4) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53.45% | With copper(l) iodide; 8-quinolinol; potassium carbonate; In dimethyl sulfoxide; at 130℃; for 12h;Inert atmosphere; | General procedure: Compound 1 (5g, 22.83mmol) was dissolved in DMSO (120mL), followed by the addition of 2-Piperidinone (4.53g, 45.66mmol), CuI (0.43g, 2.28mmol), 8-hydroxy-quinoline (0.66g, 4.57mmol) and K2CO3 (9.46g, 68.49mmol). The mixture was heated to 130C under N2 for 12h, cooled, and quenched with water (120mL). The organics were extracted with ethyl acetate (2×150mL) and dried (Na2SO4). Purification by silica gel column chromatography (n-hexane/ethyl acetate, 5/1 to 3/1, as eluent) afforded compound 2 as faint yellow (2.80g, 64.47%). |
50% | With copper(l) iodide; N,N-dimethyl-formamide; at 120℃;Inert atmosphere; | Under nitrogen, 8 (21.3 g, 0.21 mol), K3C0349.2 g,Catalytic amount of Cul,P-iodoaniline (35.5 g, 0.16 mil) was added to DMF and heated to 120 C. The color of the reaction solution was gradually changed from yellow to dark brown. Reaction time 30 ~ 40h. The reaction is completed, add anhydrous methanol 142ml, reflux lh, hot filter, evaporated the filtrate, add 355ml water, stirring lh, filter, evaporated the filtrate, add 142ml anhydrous ethanol, activated carbon decolorization, reflux lh, hot Filtration, the filtrate cooling crystallization, pale yellow solid 15.5g, yield 50%. |
With potassium carbonate; N,N`-dimethylethylenediamine;copper(l) iodide; In 1,4-dioxane; at 110℃; | To a blue solution of 3 -morpholinone (250 mg, 2.48 mmol), 4-iodoaniline (650 mg, 2.97 mmol), CuI (47 mg, 0.25 mmol) and N,N'-dimethylethylenediamine (0.040 mL, 0.372 mmol) in dioxane (5 mL) in a pressure bottle, K2CO3 (683 mg, 4.95 mmol) was added. The mixture was heated at 110 0C overnight. After being cooled to room temperature, the crude dark solution was loaded to two preparative TLC plates, eluted with EtOAc/MeOH (95/5) to give the desired product as off-white solid (240 mg). MS 193.l (M+H). |
With potassium carbonate;copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110℃; | B. Preparation of 4-(3-oxo-morpholin-4-yl)phenylamine;[0440] To a blue solution of <strong>[109-11-5]3-morpholinone</strong> (250 mg, 2.48 mmol), 4-iodoaniline (650 mg, 2.97 mmol), CuI (47 mg, 0.25 mmol) and N,N'-dimethylethylenediamine (0.040 mL, 0.372 mmol) in dioxane (5 mL) in a pressure bottle, K2CO3 (683 mg, 4.95 mmol) was added. The mixture was heated at 110 C overnight. After being cooled to room temperature, the crude dark solution was loaded to two preparative TLC plates, eluted with EtOAc/MeOH (95/5) to give the desired product as off-white solid (240 mg). MS 193.1 (M+H). | |
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110℃; | A. Preparation of 4-(3-oxo-morpholin-4-yl)phenylamine; [0169] NaH (60%, 3.2 g, 80 mmol) in a flask was washed with hexane. To the flask cooled in an ice-bath, a solution of ethanolamine (4.4 mL, 73 mmol) in dioxane (40 mL) was added. The mixture was heated at reflux for 10 min until no H2 gas evolved. The thick slurry was then cooled in an ice-bath, and a solution of ethyl chloroacetate (8.9 g, 73 mmol) in dioxane (15 mL) was added. The reaction mixture was heated at reflux for Ih. It was then filtered. The filtrate was concentrated in vacuo to give an oil, which was purified by a short flash column, eluted with EtOAc/MeOH (95/5) to give a white solid (1.9 g), as 3-morphorinone.[0170] To a blue solution of <strong>[109-11-5]3-morpholinone</strong> (250 mg, 2.48 mmol), 4-iodoaniline (650 mg, 2.97 mmol), CuI (47 mg, 0.25 mmol) and N,N'-dimethylethylenediamine (0.040 mL, 0.372 mmol) in dioxane (5 mL) in a pressure bottle, K2CO3 (683 mg, 4.95 mmol) was added. The mixture was heated at 110 C overnight. After being cooled to room temperature, the crude dark solution was loaded to two preparative TLC plates, eluted with EtOAc/MeOH (95/5) to give the desired product as off-white solid (240 mg). MS 193.1 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate; trans-1,2-cyclohexanediamine;copper(l) iodide; In 1,4-dioxane; at 110℃; | A mixture of 4-bromopyridine hydrochloride (778 mg, 4.00 mmol), <strong>[109-11-5]3-morpholinone</strong> (404 mg, 4.00 mmol), K3PO4 (1.70 g, 8.00 mmol) and 1,2-trans-diaminocyclohexane (200 uL, 1.60 mmol) in dioxane (10 mL) was degassed with Ar before being charged with CuI (152 mg, 0.80 mmol). The mixture in a sealed tube was heated at 110 0C overnight. The mixture was applied to a silica gel column, which was then eluted with 2-5% MeOH in CH2Cl2 to give the desired product (85 mg). MS 179.5 (M+H) | |
With potassium phosphate;copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; at 110℃;Heating in a sealed tube; | EXAMPLE 142 Preparation of (2R) 4-(3-morpholinon-4-yi)piperidin-l-yl-2-phenyl-2-(4- chlorophenylaminocarbonylamino)-acetamide; A. Preparation of 4-(3-morpholinon-4-yl)piperidine; [0509] A mixture of 4-bromopyridine hydrochloride (778 mg, 4.00 mmol), <strong>[109-11-5]3-morpholinone</strong> (404 mg, 4.00 mmol), K3PO4 (1.70 g, 8.00 mmol) and 1,2-trans-diaminocyclohexane (200 uL, 1.60 mmol) in dioxane (10 mL) was degassed with Ar before being charged with CuI (152 mg, 0.80 mmol). The mixture in a sealed tube was heated at 110 0C overnight. The mixture was applied to a silica gel column, which was then eluted with 2-5% MeOH in CH2Cl2 to give the desired product (85 mg). MS 179.5 (M+H).[0510] A solution of the compound (85 mg, 0.48 mmol) and PtO2 (50 mg) in HOAc (8 mL) was hydrogenated under 40 psi on a Parr shaker overnight. The mixture was filtered through Celite. The filtrate was concentrated in vacuo. To the residue, aqueous IN HCl (3 mL) was added. The solution was then concentrated in vacuo to give the desired product as hydrochloride salt (91 mg). MS 185.2 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | To a solution of ethanolamine (197 mmol, 1.1 equiv) in i-PrOH (100 mL) was portionwise added small pieces ofsodium (197 mmol, 1.1 equiv). The mixture was heated at 50 C for 5 h, and the resulting yellow solution was cooled in an ice-water bath. Ethyl chloroacetate (179 mmol, 1.0equiv) was dropwise added at 0 C, and the resulting yellow suspension was heated at 80 C for 2 h. Insoluble materials were removed by paper filtration and washed with i-PrOH. The combined filtrate and washings were concentrated in vacuo, and the resulting brown solids were recrystallized from iPrOH/EtOAc to afford 3-morpholinone in 52% yield. | |
36% | Under nitrogen, Na (45.26 g, 1.97 mol)Was added in portions to a mixed solution of dioxane and isopropanol, and the temperature was raised to 50 C to promote the dissolution of Na(Na dissolves very slowly, generally takes 4 to 5 hours).After all the Na is dissolved,Dropping amino ethanol (98ml, 1.67mo) 1, drop Bi, 50 C stirring 30 ~ 40min.Was transferred to cold water, controlled at -10 C, and ethyl chloroacetate (182 ml, 1.75mo 1) was added dropwise. Drop 10 C stirring 30 ~ 40min.Gradually heated to 80 C, the reaction about 10h, finished, hot filter, the filtrate evaporated to dry yellow oily liquid, dissolved with ethyl acetate, standing, the above clear ethyl acetate layer out of cooling crystallization,To be precipitated after the white needle-like crystals after filtration, to obtain moles of crude ketone. The remaining yellow oil was recrystallized again as described above in a yield of 36% | |
Ethanolamine is reacted in the presence of sodium hydride with ethyl chloroacetate to give morpholin-3-one (m.p. 100-102 C.) and the desired acid obtained therefrom by heating with barium hydroxide and subsequent treatment with sulphuric acid. |
EXAMPLE 95; N-[4-(3-oxo-morpholin-4-yl)phenyl]-2-(2-methylphenyl)-2-(4- chlorophenylaminocarbonylamino)-acetamide; A. Preparation of 3 -morpholinone; EPO <DP n="100"/>[0439] NaH (60%, 3.2 g, 80 mmol) in a flask was washed with hexane. To the flask cooled in an ice-bath, a solution of ethanolamine (4.4 mL, 73 mmol) in dioxane (40 mL) was added. The mixture was heated at reflux for 10 min until no H2 gas evolved. The thick slurry was then cooled in an ice-bath, and a solution of ethyl chloroacetate (8.9 g, 73 mmol) in dioxane (15 mL) was added. The reaction mixture was heated at reflux for Ih. It was then filtered. The filtrate was concentrated in vacuo to give an oil, which was purified by a short flash column, eluted with EtOAc/MeOH (95/5) to give a white solid (1.9 g). | ||
A. Preparation of 4-(3-oxo-morpholin-4-yl)phenylamine; [0169] NaH (60%, 3.2 g, 80 mmol) in a flask was washed with hexane. To the flask cooled in an ice-bath, a solution of ethanolamine (4.4 mL, 73 mmol) in dioxane (40 mL) was added. The mixture was heated at reflux for 10 min until no H2 gas evolved. The thick slurry was then cooled in an ice-bath, and a solution of ethyl chloroacetate (8.9 g, 73 mmol) in dioxane (15 mL) was added. The reaction mixture was heated at reflux for Ih. It was then filtered. The filtrate was concentrated in vacuo to give an oil, which was purified by a short flash column, eluted with EtOAc/MeOH (95/5) to give a white solid (1.9 g), as 3-morphorinone.[0170] To a blue solution of 3-morpholinone (250 mg, 2.48 mmol), 4-iodoaniline (650 mg, 2.97 mmol), CuI (47 mg, 0.25 mmol) and N,N'-dimethylethylenediamine (0.040 mL, 0.372 mmol) in dioxane (5 mL) in a pressure bottle, K2CO3 (683 mg, 4.95 mmol) was added. The mixture was heated at 110 C overnight. After being cooled to room temperature, the crude dark solution was loaded to two preparative TLC plates, eluted with EtOAc/MeOH (95/5) to give the desired product as off-white solid (240 mg). MS 193.1 (M+H). | ||
500 mg | under a nitrogen atmosphere, sodium hydride (60 wt %, 1.2 g) and a solution of dioxane (25 ml) was cooled to 0 C, ethanolamine (1.5 ml) was added at room temperature and stirred for 30 minutes. This reaction liquid is cooled to 0 C, after 30 minutes stirring at room temperature ethyl chloroacetate (2.7 ml) was added, this reaction mixture was further stirred and heated for 40 minutes under reflux condition. After cooling the reaction liquid, solid is removed by filtration. Under a reduced pressure by concentrating somas, refining residues is obtained in column chromatography (ethyl acetate: methanol = 19:1), obtained as a colorless solid morpholin-3-one (500 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; N,N`-dimethylethylenediamine;copper(l) iodide; In 1,4-dioxane; at 140℃; for 12h;Microwave synthesizer; | Example 114-(8-[(2,6-Dimethylphenyl)methyl|amino}-2,3-dimethylimidazo[l,2-α]pyridin-6- yl)-<strong>[109-11-5]3-morpholinone</strong> hydrochlorideA mixture of 6-bromo-N-[(2,6-dimethylphenyl)methyl]-2,3-dimethylimidazo[ 1 ,2- α]pyridin-8-amine (100 mg, 0.28 mmol; WO 98/37080), <strong>[109-11-5]3-morpholinone</strong> (56 mg, 0.56 mmol; US 3308121), copper(I) iodide (16 mg, 0.083 mmol), potassium carbonate (138 mg, 1.0 mmol) and ΛζN'-dimethylethylenediamine (7.4 mg, 0.083mmol) in dioxane (2 mL) was heated in an Initiator Microwave Synthesizer at 140C for 12 hours. The cooled mixture was applied to an Isolute SCX cartridge. Elution with methanol, followed by water, then methanol then IM NH3 in methanol gave, after evaporation, the product which was further purified by chromatography on silica gel. Elution with dichloromethane/methanol (0 to 10%) gave a pale yellow solid which was dissolved in methanol (2 mL), Ethereal HCl (IM; 0.3ml) was added and the solvent evaporated to give the title compound as a pale yellow solid; MS (ES+ve): [M+H]+ at m/z 379 (C22H26N4O2 requires [M+H]+ at m/z 379). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; N,N`-dimethylethylenediamine;copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 120℃; for 18h;Microwave synthesizer; | Description 12 4-[2,3-Dimethyl-8-({ [4-(methyloxy)phenyl] methyI}oxy)imidazo[l,2-α]pyridin-6-A mixture of 6-bromo-2,3-dimethyl-8-([4-(methyloxy)phenyl]methyl} oxy)imidazo[l,2-α]pyridine (589 mg, 1.63 mmol; Description 5), 3-moφholinone (330 mg, 3.27 mmol; US 3308121), cesium carbonate (1.86 g, 5.7 mmol), copper(I) iodide (89 mg, 0.47 mmol) and ΛζN'-dimethylethylenediamine (42 mg, 0.47 mmol) in N-methylpyrrolidinone (10 mL) was heated in an Initiator Microwave Synthesizer at 120C for 18 hours. The mixture was applied to an Isolute SCX cartridge and washed with methanol followed by elution with 2M NH3 in methanol. The basic fractions were combined and evaporated under reduced pressure. This residue was purified by column chromatography on silica eluting with a 50-100% ethyl acetate in hexane gradient to afford the title compound. MS (ES+ve): [M+H]+ at m/z 382 (C2]H23N3O4 requires [M+H]+ at m/z 382). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | To a suspension of morpholin-3-one (29 mg, 0.288 mmol) in THF (2 mL) was added NaH (16.14 mg, 0.336 mmol). After stirring the mixture for 5 mi (3- (bromomethyl)phenyl)boronic acid (41.3 mg, 0.192 mmol) was added and the resulting mixture was stirred at room temperature for 2 h. Water (1 mL) was added, followed byphosphoric acid, potassium salt (61.2 mg, 0.288 mmol) and 7-bromo-5-(1-(tetrahydro-2H-pyran-4-yl)- 1 H- 1,2,3 -triazol-5-yl)pyrrolo[2, 1 -f] [1 ,2,4]triazin-4-amine (35 mg, 0.096 mmol). The reaction vessel was evacuated, backfilled with N2 and then degassed by bubbling N2 while being sonicated. Tetrakis triphenylphosphine (11.11 mg, 9.61 .imol) was added and the degassing process was repeated. The reaction mixture was heated at140 C in a microwave for 1 h. The reaction mixture was cooled, filtered, washed with water and extracted with ethyl acetate (10 mL x 3). The organic layers were combined, dried and concentrated. The residue purified by preparative LCMS method C to obtain 4-(3 -(4-amino-5-( 1 -(tetrahydro-2H-pyran-4-yl)- 1 H- 1,2,3 -triazol-5 -yl)pyrrolo[2, 1 -f] [1,2,4] triazin-7-yl)benzyl)morpholin-3-one (5.3 mg, 11% yield). LC/MS (M+H) =475.15. ?H NMR (500 MHz, DMSO-d6) oe 2.0 (m, 2H), 2.16 (m, 2H), 3.32 (t, 2H), 3.37 (m, 2H), 3.85 (t, 2H), 3.93 (m, 3H), 4.14(s, 2H), 4.64 (s, 2H), 7.27 (m, 2H), 7.50 (t, 1H), 7.87 (s, 1H), 7.96 (m, 2H), 8.10 (m, 1H). |
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