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[ CAS No. 73931-63-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 73931-63-2
Chemical Structure| 73931-63-2
Chemical Structure| 73931-63-2
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Product Details of [ 73931-63-2 ]

CAS No. :73931-63-2 MDL No. :MFCD17018863
Formula : C9H7NO2S Boiling Point : -
Linear Structure Formula :- InChI Key :ISXQEAJOCDXKAU-UHFFFAOYSA-N
M.W : 193.22 Pubchem ID :595763
Synonyms :

Calculated chemistry of [ 73931-63-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.9
TPSA : 67.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.08
Log Po/w (MLOGP) : 1.35
Log Po/w (SILICOS-IT) : 2.96
Consensus Log Po/w : 2.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.82
Solubility : 0.29 mg/ml ; 0.0015 mol/l
Class : Soluble
Log S (Ali) : -3.28
Solubility : 0.101 mg/ml ; 0.000523 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.05
Solubility : 0.173 mg/ml ; 0.000893 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 73931-63-2 ]

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 [ 73931-63-2 ]

* 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 [ 73931-63-2 ]
  • Downstream synthetic route of [ 73931-63-2 ]

[ 73931-63-2 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 3622-35-3 ]
  • [ 18107-18-1 ]
  • [ 73931-63-2 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 0 - 20℃;
Stage #2: With acetic acid In methanol; dichloromethane for 0.5 h;
Benzothiazole-6-carboxylic acid (71a, 5.0 g, 27.93 mmol) was dissolved in DCM (96 mL) and MeOH (32 mL) and cooled to 0° C. A solution of trimethylsilyl-diazomethane (28 mL, 2.0M in hexane) was added dropwise and the resulting solution was gradually warmed to RT and stirred overnight. The reaction was quenched slowly by careful addition of HOAc (2 mL) and stirred for 30 min. The solution was concentrated, diluted with EtOAc and washed with saturated NaHCO3 solution. The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatographed eluting with 15percent EtOAc/hexane to afford 4.44 g (82percent) of 71b as a white solid: 1H NMR (300 MHz, CDCl3): 9.15 (s, 1H), 8.68 (m, 1H), 8.16 (m, 2H), 3.97 (s, 3H).
Reference: [1] Patent: US2006/40927, 2006, A1, . Location in patent: Page/Page column 38
  • 2
  • [ 186581-53-3 ]
  • [ 3622-35-3 ]
  • [ 73931-63-2 ]
YieldReaction ConditionsOperation in experiment
96% at 0 - 20℃; for 1 h; Methyl benzothiazole-6-carboxylate S2b[0131] A 0.2 M stirring solution of benzothiazole-6-carboxylic acid in THF (17 mL) was cooled to 0 0C. Excess diazomethane was introduced in situ from Diazald (2.51 g, 11.7 mmol), according to literature procedure. Lombardi, P. Chem. Ind. (London) 1990, 708. After addition of the diazomethane, the solution was stirred at 0 0C for 30 min and then at room temperature for 30 min. The solvent was removed under reduced pressure to afford 0.621 g (96percent) of S2b as a tan solid, mp 105-106 0C. 1H NMR (400 MHz, CDCl3): δ 3.95 (s, 3H), 8.13-8.18 (m, 2H), 4), 7.93 (dd, IH, J= 0.8, 1.2), 9.14 (s, IH). 13C-NMR (100 MHz, <n="51"/>CDCl3): δ 52.6, 123.6, 124.4, 127.5, 127.6, 133.9, 156.2, 157.5, 166.7. HRMS-FAB (m/z): [MH]+ calcd for C9H8NO2S, 194.0276; found, 194.0270.
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6404 - 6410
[2] Patent: WO2009/75778, 2009, A2, . Location in patent: Page/Page column 49-50
  • 3
  • [ 67-56-1 ]
  • [ 3622-35-3 ]
  • [ 73931-63-2 ]
YieldReaction ConditionsOperation in experiment
79% at 60℃; for 2 h; Inert atmosphere To a mixture of benzo[d]thiazole-6-carboxylic acid (10 g, 56 mmol) in anhydrous methanol (100 mL) was added thionyl chloride (21 g, 0.18 mol) slowly at room temperature. The mixture was heated to 60 °C and stirred under nitrogen for 2 hours. On completion, the mixture was concentrated in vacuo. The residue was diluted with water (100 mL) and extracted with dichloromethane (3 100 mL). The combined organic layers were concentrated in vacuo give compound B-182 (8.5 g, 79percent yield) as a brown solid.
Reference: [1] Patent: WO2015/66371, 2015, A1, . Location in patent: Paragraph 00364-00365
[2] Patent: US2005/209274, 2005, A1, . Location in patent: Page/Page column 35-36
  • 4
  • [ 66947-92-0 ]
  • [ 73931-63-2 ]
Reference: [1] Synthetic Communications, 1980, vol. 10, # 3, p. 167 - 174
  • 5
  • [ 2942-15-6 ]
  • [ 73931-63-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1191,1195; engl. Ausg. S. 1235, 1239
  • 6
  • [ 3622-35-3 ]
  • [ 73931-63-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1191,1195; engl. Ausg. S. 1235, 1239
  • 7
  • [ 23451-96-9 ]
  • [ 73931-63-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1191,1195; engl. Ausg. S. 1235, 1239
  • 8
  • [ 67-56-1 ]
  • [ 55439-73-1 ]
  • [ 73931-63-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1950, vol. 20, p. 1191,1195; engl. Ausg. S. 1235, 1239
[2] Journal of the Chemical Society, 1949, p. 355,361
  • 9
  • [ 73931-63-2 ]
  • [ 19989-67-4 ]
Reference: [1] Patent: WO2015/66371, 2015, A1,
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