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[ CAS No. 677304-83-5 ] {[proInfo.proName]}

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Chemical Structure| 677304-83-5
Chemical Structure| 677304-83-5
Structure of 677304-83-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 677304-83-5 ]

CAS No. :677304-83-5 MDL No. :MFCD13195419
Formula : C8H5NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :ORSZGLLQNYSMNO-UHFFFAOYSA-N
M.W : 179.20 Pubchem ID :45076984
Synonyms :

Calculated chemistry of [ 677304-83-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.58
TPSA : 78.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : 1.03
Log Po/w (SILICOS-IT) : 2.49
Consensus Log Po/w : 1.75

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.64
Solubility : 0.413 mg/ml ; 0.00231 mol/l
Class : Soluble
Log S (Ali) : -3.17
Solubility : 0.121 mg/ml ; 0.000676 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.34
Solubility : 0.815 mg/ml ; 0.00455 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 677304-83-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 677304-83-5 ]

* 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.

  • Upstream synthesis route of [ 677304-83-5 ]
  • Downstream synthetic route of [ 677304-83-5 ]

[ 677304-83-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 677304-90-4 ]
  • [ 677304-83-5 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 4 h; Aqueous sodium hydroxide (50percent, 10 mL) was added to a 0 C solution of ethyl 1,3-benzothiazole-7-carboxylate (3.5 g, 16.89 mmol) in a mixture of methanol (65 mL), tetrahydrofuran (20 mL) and water (5 mL). The mixture was maintained at room temperature for 4 h and the volatiles were removed under reduced pressure. The residue was dissolved in water (100 mL) and concentrated hydrochloric acid was added to adjust pH of the solution to 5. The mixture was cooled to 0 C and maintained for 30 min. The product was isolated by filtration, washed with water (10 mL), and dried in vacuum oven (70 C) overnight to yield 2.75 g (91percent) of the acid. 1H NMR (500 MHz, DMSO-d6) delta; 7.71 (t, J= 7.5, 1H), 8.15 (d, J= 7, 1H), 8.38 (d, J= 8, 1H), 9.51 (s, 1H), 13.74 (bs, 1H); MS (APCI) m/z 178 (M+ -1)
91%
Stage #1: With sodium hydroxide; water In tetrahydrofuran; methanol at 0 - 20℃; for 4 h;
Stage #2: With hydrogenchloride In water at 0℃; for 0.5 h;
A solution of ethyl 3-aminobenzoate (90 mmol) in chlorobenzene (100 mL) was cooled to-10 °C and treated with sulfuric acid (45 mmol), dropwise. After 15 min, solid potassium thiocyanate (95 mmol) was added in several portions over 30 min followed by 18-crown-6 (250 mg). The mixture was heated at 100 °C for 10 h, allowed to cool to rt, and was maintained for an additional 4 h. The precipitated solids were isolated by filtration and were washed successively with chlorobenzene (25 mL) and hexanes (3 x 100 mL). The solid was suspended in water (300 mL) and the suspension was maintained 30 min. The product was isolated by filtration and washed with water (2 x 100 mL). The product was dried in a vacuum oven (55 °C) for 16 h, thus providing the thiocarbamate in 69percent yield.'H NMR (500 MHz, Me2SO-d6) 5 1.32 (t, J= 7.5, 3H), 4.32 (q, J = 7, 2H), 7.44-7. 47 (m, 2H), 7.68-7. 76 (m, 3H), 8.05 (s, 1H), 9. 86 (s, 1H); MS (APCI) m/z 225 (M++1). A solution of thiocarbamate (12.2 mmol) in chloroform (10 mL) was added dropwise over a period of 40 min to a vigorously maintained mixture of ethyl 3- [(aminocarbonothioyl) amino] benzoate (5.78 mmol), glacial acetic acid (10 mL) and chloroform (10 mL). The mixture was maintained 30 min at rt and then was heated at 70 °C for 4 h. The mixture was allowed to cool to room temperature and maintained for an additional 13 h. The volatiles were removed under reduced pressure and the solid residue was suspended in a mixture of chloroform (10 mL) and acetone (10 mL). The product was isolated by filtration, washed successively. with acetone (5 mL) and hexanes (10 mL), and dried in a vacuum oven, thus providing the product in 95percent yield as a mixture of ethyl 2-amino-1, 3-benzothiazole-7-carboxylate hydrobromide and ethyl 2-amino-1, 3- benzothiazole-5-carboxylate hydrobromide in a ratio of 95/5, respectively. This product was partitioned between saturated aqueous solution of sodium bicarbonate (25 mL) and a mixture of ethyl acetate (70 mL) and tetrahydrofuran (30 mL). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated. The residue was crystallized form ethyl acetate, thus providing pure ethyl 2-amino-1, 3-benzothiazole-7- carboxylate. 1H NMR (500 MHz, Me2SO-d6) 8 1. 35 (t, J= 7.5, 3H), 4.36 (q, J= 7,2H), 7. 35 (t, J= 7. 5, 1H), 7.57 (d, J= 7, 1H), 7.61 (bs, 2H), 7.65 (d, J= 8, 1H) ; MS (EI) mlz 223 (M++1). iso-Amylnitrite (53 mmol) was added to a solution of ethyl 2-amino-1, 3-benzothiazole-7- carboxylate (5.40 g) in tetrahydrofuran (70 mL) and the mixture was heated at reflux for 4 h. The volatiles were removed under reduced pressure and the residue was purified by chromatography (0/100 to 5/95 methanol/dichloromethane), thus providing the ester in 71percent yield. lH NMR (500 MHz, CDC13) 6 1. 47 (t, J = 7. 5,3H), 4.49 (q, J= 7, 2H), 7.62 (t, J= 8, 1H), 8.20 (d, J= 6.5, 1H), 8.33 (d, J= 8, 1H), 9.12 (s, 1H); MS (EI) m/z 208 (M++1). A 50percent aqueous sodium hydroxide (10 mL) was added to a 0 °C solution of ethyl 1, 3-benzothiazole-7-carboxylate (16.89 mmol) in a mixture of methanol (65 mL), tetrahydrofuran (20 mL) and water (5 mL). The mixture was maintained at room temperature for 4 h and the volatiles were removed under reduced pressure. The residue was dissolved in water (100 mL) and concentrated hydrochloric acid was added to adjust the pH of the solution to 5. The mixture was cooled to 0 °C and maintained for 30 min. The product was isolated by filtration, washed with water (10 mL), and dried in vacuum oven (70 °C) for 16 h, thus providing the acid in 91percent yield. 1H NMR (500 MHz, Me2 S O-d6) 8 7.71 (t, J = 7.5, 1H), 8.15 (d, J = 7, 1H), 8. 38 (d, J = 8, 1H), 9. 51 (s, 1H), 13.74 (bs, 1H); MS (APCI) m/z 178 (M-1).
Reference: [1] Patent: WO2004/29050, 2004, A1, . Location in patent: Page 69
[2] Patent: WO2005/92890, 2005, A2, . Location in patent: Page/Page column 71
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  • [ 1038509-28-2 ]
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Reference: [1] Patent: WO2008/81399, 2008, A2, . Location in patent: Page/Page column 79
[2] Patent: WO2009/104155, 2009, A1, . Location in patent: Page/Page column 58-59
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  • [ 4518-10-9 ]
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Reference: [1] Patent: WO2009/104155, 2009, A1,
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  • [ 209459-11-0 ]
  • [ 677304-83-5 ]
Reference: [1] Patent: WO2009/104155, 2009, A1,
  • 5
  • [ 192948-00-8 ]
  • [ 677304-83-5 ]
Reference: [1] Patent: WO2009/104155, 2009, A1,
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