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[ CAS No. 389621-84-5 ] {[proInfo.proName]}

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Chemical Structure| 389621-84-5
Chemical Structure| 389621-84-5
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Product Details of [ 389621-84-5 ]

CAS No. :389621-84-5 MDL No. :MFCD03411952
Formula : C11H14BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KMNLIQJXZPBCDU-UHFFFAOYSA-N
M.W : 235.04 Pubchem ID :2773546
Synonyms :

Safety of [ 389621-84-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 389621-84-5 ]

* 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.

  • Downstream synthetic route of [ 389621-84-5 ]

[ 389621-84-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 389621-84-5 ]
  • [ 866758-52-3 ]
  • (4-{4-[4-(chloro-difluoro-methoxy)-phenylamino]-phthalazin-1-yl}-phenyl)-morpholin-4-yl-methanone [ No CAS ]
  • 2
  • [ 389621-84-5 ]
  • [ 949557-71-5 ]
  • [ 949557-72-6 ]
YieldReaction ConditionsOperation in experiment
81% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 70℃; for 1 - 18h; Step B: Preparation of N-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide: To a small round bottom flask was added N-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (30 mg, 0.0425 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (20.0 mg, 0.0849 mmol), and Pd(PPh3)4 (2.45 mg, 0.00212 mmol) and the mixture was dissolved in 3:1 DME:aqueous 2N Na2CO3 (2 mL). The mixture was stirred at 70 C. until the reaction was determined to be complete by LC/MS (1-18 hours). The reaction mixture was then partitioned between ethyl acetate (15 mL) and water (30 mL). The organic layer washed with brine, dried over Na2SO4 and evaporated to afford crude product. Purified by silica gel column chromatography (Biotage 12M) eluding with 1-5% MeOH/CHCl3 to give the desired product. Yield: 40.2 mg, 81%. LRMS (APCI pos) m/e 770.1 (M+H).
  • 3
  • [ 389621-84-5 ]
  • [ 949558-32-1 ]
  • [ 949558-33-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 1h; Step F: Preparation of 5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one: A suspension of 5-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.013 g, 0.019 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.005 g, 0.02 mmol), Pd(PPh3)4 (0.001 g, 0.0009 mmol) and lithium chloride (0.003 g, 0.08 mmol) in dioxane (0.5 mL) and 2 M aqueous Na2CO3 (0.5 mL) was stirred at 100 C. for 1 hour. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated to yield 0.014 g crude product as a yellow gum. The crude material was used without further purification in the following step. LRMS (APCI pos) m/e 738 (M+1).
  • 4
  • [ 389621-84-5 ]
  • [ 949556-71-2 ]
  • [ 949558-41-2 ]
YieldReaction ConditionsOperation in experiment
12% Step C: Preparation of (4-(4-(4-amino-2-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)phenyl)(morpholino)methanone: A mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (0.30 g, 0.612 mmol; prepared as in Example 7, Step B), Cs2CO3 (0.299 g, 0.918 mmol), and <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.151 g, 0.643 mmol) in DME (3 mL) was degassed under nitrogen for 10 minutes and tetrakistriphenylphosphinepalladium (0.035 g, 0.03 mmol) was added. The reaction mixture was heated at 85 C. for 15 hours. The precipitate was removed by filtration with a mixture of EtOAc and MeOH. The filtrate was concentrated and the crude material was purified by silica gel flash column chromatography (1% MeOH in CH2Cl2) to afford 39 mg (12%) of the desired product. LRMS (APCI pos) m/e 554.1 (M+1).
  • 5
  • [ 389621-84-5 ]
  • [ 949558-52-5 ]
  • [ 949558-53-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 20 - 100℃; Step E: Preparation of 2-(cyclohexylmethyl)-5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one: A suspension of 2-(cyclohexylmethyl)-5-(3-fluoro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methylpyrimidin-4(3H)-one (0.025 g, 0.037 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.010 g, 0.044 mmol), Pd(PPh3)4 (0.002 g, 0.002 mmol) and lithium chloride (0.006 g, 0.147 mmol) in dioxane (1 mL) and 2 M aqueous Na2CO3 (1 mL) was stirred at 100 C. for 35 minutes and then at room temperature overnight. The reaction mixture was partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1*). The combined organic layers were dried over Na2SO4, filtered and concentrated to yield 0.027 g crude product as a yellow gum. The crude material was used without further purification in the following step. LRMS (APCI pos) m/e 743 (M+1).
  • 6
  • [ 389621-84-5 ]
  • [ 344940-69-8 ]
  • 4-{3-amino-6-[4-(morpholin-4-ylcarbonyl)phenyl]pyrazin-2-yl}phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120℃; for 0.25h;Microwave; 4-(2-amino-5-bromopyrazin-3-yl)phenol (15 mg, 0.06 mmol), [4-(Morpholine-4- carbonyl)phenyl]boronic acid (20.2 mg, 0.086 mmol), tetrakis(triphenylphosphine)palladium (4 mg, 0.0034 mmol) and Na2COa (aq) (0.2 ml, 0.2 mmol) were suspended in DME (1 ml) and heated in the microwave to 1200C for 15 minutes. The mixture was evaporated and dissolved in MeOH ( 1 ml) and purified by reversed phase preparative HPLC using XTerra Prep MS C 18 5mum 19 x 50 mm, flow 25 ml/min, 50 mM pH IO NH4HCO3 / ACN, fractions collected based on UV-signal (254 nm). Yield: 3.2 mg (15%). Light yellow solid. MS (electronspray) M+H+ m/z 377.1.
  • 7
  • [ 389621-84-5 ]
  • [ 1000068-47-2 ]
  • 4-{6-[4-(morpholin-4-ylcarbonyl)phenyl]pyrazin-2-yl}phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 130℃; for 0.166667h;Microwave; 4-(6-chloropyrazin-2-yl)phenol (200 mg, 0.97 mmol), 4-(Morpholine-4- carbonyl)phenyl]boronic acid, (300 mg, 1.27 mmol), tetrakis(triphenylphosphine)palladium (20 mg, 0.017), NaHCO3 (200 mg, 2.38 mmol) and water (1 ml) were suspended in DME (3 ml) and heated to 1300C for 10 minutes in the microwave. The mixture was diluted with dichloro- methane, filtered and transferred to a separation funnel. The organic phase was washed with water (Ix), brine (Ix), dried (MgSC^) and evaporated. The crude product was purified by suspending it with dichloromethane (sparingly soluble) and filtered. The grey powder was washed with dichloromethane (2x) and dried in vacuo. Yield 1 18 mg (33%). Grey solid. HPLC 96% Rt= I .74 (system A. 10-97% MeCN over 3 minutes). HPLC 95% Rt=I .62 (system B. 10-97% MeCN over 3 minutes). MS (electronspray; [M+H]+) m/z 362.4.IH NMR (400 MHz, DMSO-D6) delta ppm 3.49 - 3.75 (m, 6 H) 6.93 (d, J=8.78 Hz, 2 H) 7.58 (d, J=8.28 Hz, 2 H) 8.13 (d, J=8.78 Hz, 2 H) 8.30 (d, J=8.53 Hz, 2 H) 9.13 (s, 2 H) 9.95 (s, 1 H).
  • 8
  • [ 389621-84-5 ]
  • [ 850727-85-4 ]
  • 4-[(aminocarbonyl)amino]-1-[4-(morpholin-4-yl-carbonyl)phenyl]-1H-pyrazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper diacetate; In dichloromethane; [00714] Example 9: 4- [ (aminocarbonyl) amino]-l- [4- (morpholin-4-yl- carbonyl) phenyl]-1 H-pyrazole-3-carboxamide; [00716] A suspension of 4-[(aminocarbonyl) amino]-1 H-pyrazole-3- carboxamide (150 mg, 0.89 mmol) (prepared according to Example 19, from 4- amino-1 H-pyrazole-3-carboxamide, see J. Am. Chem. Soc. 78, 2418-2422 (1956) ) in pyridine (2.0 mL) and CH2CI2 (1. 0 mL) was treated with 4- (morpholine- 4-carbonyl) phenylboronic acid (208 mg, 0.89 mmol) and Cu (OAc) 2 (161 mg, 0.89 mmol). The reaction was stirred under nitrogen overnight. The crude mixture was concentrated, and redissolved in DMF (2 mL). The reaction mixture was then filtered through a syringe filter (0. 45 um), purified by prep. rpHPLC, and lyophilized to give the title compound as a white solid. ESI mass spectrum for C16H19N6O4+: 359.18 (M+1).
  • 10
  • [ 389621-84-5 ]
  • [ 874347-40-7 ]
  • C35H47N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In ethanol; at 120℃; for 0.333333h;Microwave; A tube containing 82 (30 mg), 4-(4-morpholinocarbonyl)phenylboronic acid (263 mg), Pd(Ph3P)2Cl2 (2 mg) and NEt3 (31 muL) in EtOH (900 muL) was sealed and heated in the microwave at 120 C. during 20 mins. The reaction mixture was added to silica gel (1 g) and the solvent allowed to evaporate; purification of the residue by silica gel chromatography (50->100% EtOAc/hexanes) gave 109 as a clear colorless oil, 14 mg. MS (ESI(+)) m/e 606.4 (M+H)+.
  • 11
  • [ 389621-84-5 ]
  • [ 918643-41-1 ]
  • (4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)(morpholino)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 85℃; for 18h; Example 130; N-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide; Step A: Preparation of (4-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)phenyl)(morpholino)methanone; A sealable tube was charged with 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)aniline (Example 6, Step A, 0.200 g, 0.518 mmol), cesium carbonate (0.253 g, 0.777 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.183 g, 0.777 mmol) and DME (2 mL). The mixture was degassed under nitrogen for 10 minutes and Pd(PPh3)4 (0.0299 g, 0.0259 mmol) was added as a solid. The mixture was heated to 85 C. for 18 hours. The crude was diluted with water (300 mL), extracted with EtOAc/MeOH (4:1, 2×300 mL), dried organic over sodium sulfate, filtered and concentrated. The crude product was purified by preparative TLC (2.0 mm thickness) eluting with EtOAc/MeOH (9:1) to give product (31 mg, 12%) as a white solid. LRMS (APCI+) 450 m/z (M+1) detected.
  • 12
  • [ 389621-84-5 ]
  • [ 946505-31-3 ]
  • 5-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 0.5h; Example 144; 5-(3-fluoro-4-(2-(4-(morpholine-4-carbonyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one; A suspension of 5-(3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (Example 143, Step F, 0.018 g, 0.0316 mmol), <strong>[389621-84-5]4-(morpholine-4-carbonyl)phenylboronic acid</strong> (0.009 g, 0.038 mmol), Pd(PPh3)4 (0.002 g, 0.002 mmol) and lithium chloride (0.005 g, 0.126 mmol) in dioxane (1 mL) and 2 M aqueous Na2CO3 (1 mL) was stirred at 100 C. for 30 minutes. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and H2O. The layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by flash column chromatography, eluting with 10:1 CH2Cl2/MeOH. The product was obtained (12.9 mg; 65%) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 9.04 (br s, 1H), 8.55 (d, 1H), 8.17 (s, 1H), 8.12 (s, 1H), 7.99 (m, 2H), 7.89 (dd, 1H), 7.69 (m, 1H), 7.58-7.49 (m, 5H), 7.38 (m, 2H), 7.17 (m, 1H), 6.70 (dd, 1H), 3.63 (m, 8H), 3.59 (s, 3H). LRMS (APCI pos) m/e 634 (M+1).
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