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[ CAS No. 4576-90-3 ] {[proInfo.proName]}

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Chemical Structure| 4576-90-3
Chemical Structure| 4576-90-3
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Quality Control of [ 4576-90-3 ]

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Product Details of [ 4576-90-3 ]

CAS No. :4576-90-3 MDL No. :MFCD09834765
Formula : C4H3NO2S Boiling Point : No data available
Linear Structure Formula :- InChI Key :BMPVWNJQCJQBFW-UHFFFAOYSA-N
M.W : 129.14 Pubchem ID :559224
Synonyms :

Calculated chemistry of [ 4576-90-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.07
TPSA : 78.43 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.81
Log Po/w (XLOGP3) : 0.84
Log Po/w (WLOGP) : 0.84
Log Po/w (MLOGP) : -0.77
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 0.66

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.57
Solubility : 3.51 mg/ml ; 0.0271 mol/l
Class : Very soluble
Log S (Ali) : -2.07
Solubility : 1.1 mg/ml ; 0.00851 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.63
Solubility : 30.3 mg/ml ; 0.235 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.93

Safety of [ 4576-90-3 ]

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

Application In Synthesis of [ 4576-90-3 ]

* 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 [ 4576-90-3 ]

[ 4576-90-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 693-92-5 ]
  • [ 4576-90-3 ]
YieldReaction ConditionsOperation in experiment
23% With chromium(VI) oxide; sulfuric acid; at 0 - 20℃; for 16h;Inert atmosphere; To a stirred solution of compound 39 (10 g, 100.85 mmol) in concentrated sulfuric acid (300 mL) under inert atmosphere was added chromium (VI) oxide (30.25 g, 302.57 mmol) portion wise at 0 oC, followed by warming to room temperature and stirring for 16 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with ice-cold water (3 L) slowly and extracted with diethyl ether (10 x 600 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford crude compound 40 (3 g, 23%) as white solid. TLC: 20% EtOAc/ hexanes (Rf: 0.1).1H-NMR (DMSO-d6, 400 MHz): delta 10.95 (br.s, 1H), 9.16 (d, J = 4.6 Hz, 1H), 7.80 (d, J = 4.6 Hz, 1H); LCMS Calculated for C4H3NO2S: 128.99; Observed: 130.4 (M+1)+.
13% With sulfuric acid; sulfur trioxide; chromium(VI) oxide; at 0 - 20℃; for 16h; Chromium(IV) oxide (9.00 mmol) is added in several batches to a solution of 3-methylisothiazole (3.03 mmol) in fuming sulfuric acid (10 ml_) at 0 0C. The reaction mixture is allowed to warm to rt and is maintained for 16 h. The reaction mixture is diluted with ice water (100 ml_), extracted with ether (6 x 200 ml_) and the combined organic layers are dried (sodium sulfate) and concentrated. The residue is purified by preparative HPLC to provide isothiazole-3-carboxylic acid in 13% yield as a white solid. 1H-NMR (400MHz, DMSO-Cf6) 5 3.43 (s, 1 H), 9.17 (d, 1 H), 7.80 (d, 1 H), 3.43 (s, 1 H); LC/MS (ES, m/z) [M+I]+ 128.
  • 2
  • [ 4576-91-4 ]
  • [ 4576-90-3 ]
YieldReaction ConditionsOperation in experiment
2.9 g. of 3-(3-Trifluoromethylphenyl)-4-amino-5-isothiazolecarboxylic acid were dissolved in 10 ml. of 1 N aqueous sodium hydroxide; Calcium chloride hydrate (0.74 g) dissolved in 3 ml. of water was added to the solution of the sodium salt. The calcium salt of the isothiazolecarboxylic acid precipitated. 50 ml. of Ethanol were added and the reaction mixture kept at ambient temperature for one hour. The mixture was poured into a mixture of ice and water. The resulting solid was filtered and air dried. Yield was 2 g. of the monohydrate calcium salt of 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxylic acid melting above 300 C. Analysis calculated for C22 H12 F6 N4 O4 S2 Ca.H2 O Theory: C, 41.77; H, 2.22; N, 8.86 Found: C, 41.31; H, 2.55; N, 8.61.
  • 5
  • [ 623155-66-8 ]
  • [ 4576-90-3 ]
  • [ 1026765-94-5 ]
YieldReaction ConditionsOperation in experiment
91% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; at 50℃; for 1h; [00163] To a solution of <strong>[4576-90-3]isothiazole-3-carboxylic acid</strong> (20 mg, 0.15 mmol), EDC (32.4 mg, 0.17 mmol), HOBt (23. mg, 0.17 mmol) in DMF (0.3 mL) was added 3- amino-N-cyclopropyl-4-methyl-benzamide hydrochloride (35 mg, 0.15 mmol) followed by DIPEA (0.03 mL, 0.17 mmol). The reaction was heated at 500C for 1 h. Water (0.6 mL) was added dropwise and the reaction removed from heating. The solids were stirred overnight at room temp, filtered, and washed with water to give (42.1 mg, 91% yield). HPLC tR= 2.63 min, 99.80 % purity; LCMS 302.1 (M + H).
  • 6
  • [ 17284-97-8 ]
  • [ 4576-90-3 ]
  • C8H4ClN5S [ No CAS ]
  • 7
  • [ 6638-79-5 ]
  • [ 4576-90-3 ]
  • N-methoxy-N-methylisothiazole-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diisopropylamine; In dichloromethane; at 20℃; for 21h;Inert atmosphere; To a solution of 500 mg (3.87 mmol) of <strong>[4576-90-3]isothiazol-3-carboxylic acid</strong> (Apollo Scientific), 415 mg (4.25 mmol) of N,O-dimethylhydroxylamine hydrochloride and 30 mg (0.196 mmol) of 1-hydroxybenzotriazole monohydrate in methylene chloride (20 ml) were added 2.7 mL (15.46 mmol) of diisopropylamine and 1.49 g (7.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide under an argon atmosphere, and the mixture was stirred at room temperature for 21 hours. After completion of the reaction, to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine, subsequently dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (elution solvent; hexane:ethyl acetate = 90:10 to 60:40 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 598 mg (3.47 mmol, yield 90%) of the title compound as a colorless oil Mass spectrum (EI, m/z): 172 [M]+. 1H-NMR spectrum (400 MHz, CDCl3) delta : 8.68 (1H, d, J = 4.6 Hz), 7.69 (1H, d, J = 4.0 Hz), 3.81 (3H, s), 3.47 (3H, brs).
63% With 4-methyl-morpholine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 16h; To a stirred solution compound 40 (3 g, 23.25 mmol) in CH2Cl2 (60 mL) under inert atmosphere were added EDCI.HCl (4.9 g, 25.58 mmol), DMAP (2.8 g, 23.25 mmol), N- methylmorpholine (7.65 mL, 69.76 mmol) and N, O-dimethylhydroxylamine hydrochloride (2.72 g, 27.90 mmol) at 0 oC, followed by warming to room temperature and stirring for 16 h. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ice-cold water and extracted with CH2Cl2. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel flash column chromatography using 40-45% EtOAc/ hexanes to afford compound 41 (2.5 g, 63%) as brown syrup. TLC: 40% EtOAc/ hexanes (Rf: 0.5); 1H NMR (400 MHz, DMSO-d6): delta 9.15 (d, J = 4.8 Hz, 1H), 7.63 (d, J = 4.4 Hz, 1H), 3.69 (s, 3H), 3.33 (s, 3H); LCMS Calculated for C6H7NOS: 141.02; Observed: 142.0 (M+1)+.LC-MS: 98.67%; 172.9 (M+1)+.
38% To a suspension of <strong>[4576-90-3]isothiazole-3-carboxylic acid</strong> (2 g, 15.49 mmol) in DCM at 0 C was added oxalyl dichloride (1.3 equiv.) followed by three drops of DMF. Bubbling commenced, and the reaction was warmed to 23 C after 10 min. The mixture was stirred for 3 h, then cooled to 0 C. N,0-dimethylhydroxylamine hydrochloride (1.3 equiv.) was added to the reaction, followed by triethylamine (3.5 equiv.) which was added dropwise via syringe over 10 min. Reactions was warm slowly to 23 C overnight, and stirred for a total of 15 h. Reaction mixture was diluted with IN HC1 solution and dichloromethane (1 :1 ratio). Layers were separated, and the aqueous layer was extracted with DCM (2x). Combined organic layers were dried over magnesium sulfate, filtered, and the solvent was removed in vacuo. Crude reside purified via silica gel chromatography (utilizing a hexane/ethyl acetate mix as eluent) to deliver the desired intermediate, N-methoxy-N-methylisothiazole-3-carboxamide (1 g, 38%> yield) as a pale yellow solid. NMR (400 MHz, CDCI3) delta ppm 8.67 (d, 1 H), 7.69 (br s, 1 H), 3.80 (s, 3 H), 3.46 (br s, 3 H).
  • 8
  • [ 4576-90-3 ]
  • [ 49672-77-7 ]
  • 9
  • [ 4576-90-3 ]
  • [ 75-65-0 ]
  • tert-butyl isothiazol-3-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With diphenyl phosphoryl azide; triethylamine; for 9h;Reflux; EXAMPLE 277 Synthesis of (S)-4-((1-benzylpyrrolidin-3-yl)(methyl)amino)-2-fluoro-//-(isothiazol-3-yl)- 5-methylbenzenesulfonamide 2,2,2-trifluoroacetate Step 1. Preparation of te/f-butyl isothiazol-3-ylcarbamate To a slurry of <strong>[4576-90-3]isothiazole-3-carboxylic acid</strong> (5.0 g, 38.7 mmol) in terf-butanol (194 mL) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenylphosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 hours. Concentration under reduced pressure provided a residue which was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), 1 N sodium hydroxide solution (50 mL), water (100 mL), and brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated in vacuo. Purification of the residue by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79 % yield): H NMR (300 MHz, CDCI3) 9.03-8.98 (m, 1 H), 8.58 (d, J = 4.9 Hz, 1 H), 7.70 (d, J = 4.9 Hz, 1 H), 1.53 (d, J = 0.7 Hz, 9H).
79% With diphenyl phosphoryl azide; triethylamine; for 9h;Reflux; To a slurry of <strong>[4576-90-3]isothiazole-3-carboxylic acid</strong> (5.0 g, 38.7 mmol) in tert-butanol (194 mL) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenyl phosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 h. After cooling the ambient temperature, the reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), 1 N sodium hydroxide solution (50 mL), water (100 mL), brine (50 mL), and dried over anhydrous magnesium sulfate. Filtration and concentration of the filtrate in vacuo afforded a residue. Purification of the residue by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79% yield): 1H NMR (300 MHz, CDCl3) delta9.03-8.98 (m, 1H), 8.58 (d, J=4.9 Hz, 1H), 7.70 (d, J=4.9 Hz, 1H), 1.53 (d, J=0.7 Hz, 9H).
79% With diphenyl phosphoryl azide; triethylamine; for 9h;Reflux; Step 1. Preparation of tert-butyl isothiazol-3-ylcarbamate To a slurry of <strong>[4576-90-3]isothiazole-3-carboxylic acid</strong> (5.0 g, 38.7 mmol) in tert-butanol (194 mL) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenylphosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 hours. Concentration under reduced pressure provided a residue which was dissolved in ethyl acetate (300 mL). The organic layer was washed with water (100 mL), 1 N sodium hydroxide solution (50 mL), water (100 mL), and brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated in vacuo. Purification of the residue by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79% yield): 1H NMR (300 MHz, CDCl3) delta 9.03-8.98 (m, 1H), 8.58 (d, J=4.9 Hz, 1H), 7.70 (d, J=4.9 Hz, 1H), 1.53 (d, J=0.7 Hz, 9H).
79% With diphenyl phosphoryl azide; triethylamine; for 9h;Reflux; To a slurry of <strong>[4576-90-3]isothiazole-3-carboxylic acid</strong> (5.0 g, 38.7 mmol) in terf-butanol (194 ml_) was added triethylamine (4.3 g, 42.6 mmol) followed by diphenyl phosphoryl azide (11.9 g, 43.3 mmol). The reaction mixture was heated to reflux for 9 hours. After cooling the ambient temperature, the reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (300 ml_). The organic layer was washed with water (100 ml_), 1 N sodium hydroxide solution (50 ml_), water (100 ml_), brine (50 ml_), and dried over anhydrous magnesium sulfate. Filtration and concentration of the filtrate in vacuo afforded a residue. Purification of the residue by column (0805) chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane, provided the title compound as a colorless solid (6.16 g, 79 % yield): 1FI NMR (300 MHz, CDCIs) 9.03-8.98 (m, 1 H), 8.58 (d, J = 4.9 Hz, 1 H), 7.70 (d, J = 4.9 Hz, 1 H), 1.53 (d, J = 0.7 Hz, 9H).

  • 10
  • [ 4576-90-3 ]
  • [ 75-65-0 ]
  • tert-butyl isothiazol-4-ylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% To a stirred suspension of <strong>[4576-90-3]isothiazole-3-carboxylic acid</strong> (10.02 g, 77.6 mmol) in anhydrous te/f-butanol (80 ml_) and anhydrous toluene (120 ml_) was slowly added triethylamine (13.0 ml_, 93.12 mmol). The mixture was stirred at ambient temperature for 5 minutes and then diphenyl phosphoryl azide (18.42 ml_, 85.36 mmol) was added dropwise to it. The reaction mixture was stirred at ambient temperature for 1 h, gradually warmed to 85 C over 1 h, and then heated at 85 C with stirring for 7 h. After cooling to ambient temperature, the reaction mixture was diluted with ethyl acetate (150 ml_) and saturated aqueous sodium bicarbonate (150 ml_). The layers were separated and the aqueous layer was extracted with ethyl acetate (2 c 100 ml_). The combined organic layers were washed with water (150 ml_), brine (150 ml_), dried over magnesium sulfate, and filtered. Concentration of the filtrate in vacuo provided a residue, which was purified by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in heptane. Further purification by column chromatography, eluting with a gradient of 0 to 10% of ethyl acetate in dichloromethane, afforded the title compound as a colorless solid (10.33 g, 66% yield): 1H NMR (400 MHz, CDCI3) d 8.56 (dd, J = 4.9, 0.6 Hz, 1 H), 8.11 (s, 1 H), 7.66 (d, J = 4.9 Hz, 1 H), 1.53 (s, 9H); MS (ES+) m/z 201.1 (M + 1).
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