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[ CAS No. 104795-85-9 ] {[proInfo.proName]}

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Chemical Structure| 104795-85-9
Chemical Structure| 104795-85-9
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Product Details of [ 104795-85-9 ]

CAS No. :104795-85-9 MDL No. :MFCD09027103
Formula : C10H7ClO2S Boiling Point : -
Linear Structure Formula :- InChI Key :YKNFICOVOXVEIN-UHFFFAOYSA-N
M.W : 226.68 Pubchem ID :18526200
Synonyms :

Calculated chemistry of [ 104795-85-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.11
TPSA : 54.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.62
Log Po/w (XLOGP3) : 3.75
Log Po/w (WLOGP) : 3.34
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 4.1
Consensus Log Po/w : 3.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.95
Solubility : 0.0253 mg/ml ; 0.000112 mol/l
Class : Soluble
Log S (Ali) : -4.59
Solubility : 0.00585 mg/ml ; 0.0000258 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.04
Solubility : 0.0206 mg/ml ; 0.0000908 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.28

Safety of [ 104795-85-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 104795-85-9 ]

* 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 [ 104795-85-9 ]
  • Downstream synthetic route of [ 104795-85-9 ]

[ 104795-85-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 104795-85-9 ]
  • [ 26018-73-5 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With lithium hydroxide; water In tetrahydrofuran at 20℃; for 4 h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
To a solution of 600 mg (3.23 mmol) of 4-chloro-2-nitro-benzaldehyde in DMF (7 ml) were added 559 mg (4.04 mmol) of potassium carbonate and 294 μl (3.23 mmol) of methyl thioglycolate at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then for 24 h at RT. Then the mixture was poured into ice-water and the precipitate was collected by filtration and dissolved in ethyl acetate. The solution was dried (MgSO4) and concentrated to yield 630 mg (86percent) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester as a white solid. 1HNMR (CDCl3, 300 MHz): δ 3.95 (s, 3H), 7.88 (dd, J=8.6 and 1.9 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.85 (d, J=1.9 Hz, 1H), 8.02 (s, 1H).To a solution of 630 mg (2.78 mmol) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester in THF (5 ml) were added 6.95 ml of 1N LiOH-solution and the reaction mixture was stirred at RT for 4 h. The pH was then adjusted to 2-3 by addition of 1N HCl and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to yield 579 mg (98percent) of 6-chloro-benzo[b]thiophene-2-carboxylic acid as white solid. MS (ISP) 211.0 (M-H)-.In analogy to example S3 (steps a to b) 139 mg (0.65 mmol) of 6-chloro-benzo[b]thiophen-2-carboxylic acid were converted into 52 mg (0.14 mmol) of (6-chloro-benzo[b]thiophen-2-ylmethyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine. The product was obtained as colorless liquid. MS (ISP) 370.0 (M+H)+.
60%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃;
To a solution of compound B-101 (10 g, 44 mmol) in tetrahydrofuran (200 mL) and water ( 10 mL) was added lithium hydroxide monohydrate (5.6 g, 0.13 mol). The reaction mixture was stirred at room temperature overnight. On completion, the reaction mixture was concentrated in vacuo to remove tetrahydrofuran and poured into water (400 mL). The pH was adjusted to 3 with 4M hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration, washed with water and dried in vacuo to give compound B-102 (5.6 g, 60percent yield) as a white solid. LCMS: (ES+) m/z (M+H)+ = 212.9.
Reference: [1] Patent: US2007/185113, 2007, A1, . Location in patent: Page/Page column 13
[2] Patent: WO2016/100184, 2016, A1, . Location in patent: Paragraph 00270
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4793 - 4807
  • 2
  • [ 5551-11-1 ]
  • [ 2365-48-2 ]
  • [ 104795-85-9 ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 24.5 h; To a solution of 600 mg (3.23 mmol) of 4-chloro-2-nitro-benzaldehyde in DMF (7 ml) were added 559 mg (4.04 mmol) of potassium carbonate and 294 μl (3.23 mmol) of methyl thioglycolate at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then for 24 h at RT. Then the mixture was poured into ice-water and the precipitate was collected by filtration and dissolved in ethyl acetate. The solution was dried (MgSO4) and concentrated to yield 630 mg (86percent) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester as a white solid. 1HNMR (CDCl3, 300 MHz): δ 3.95 (s, 3H), 7.88 (dd, J=8.6 and 1.9 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.85 (d, J=1.9 Hz, 1H), 8.02 (s, 1H).To a solution of 630 mg (2.78 mmol) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester in THF (5 ml) were added 6.95 ml of 1N LiOH-solution and the reaction mixture was stirred at RT for 4 h. The pH was then adjusted to 2-3 by addition of 1N HCl and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to yield 579 mg (98percent) of 6-chloro-benzo[b]thiophene-2-carboxylic acid as white solid. MS (ISP) 211.0 (M-H)-.In analogy to example S3 (steps a to b) 139 mg (0.65 mmol) of 6-chloro-benzo[b]thiophen-2-carboxylic acid were converted into 52 mg (0.14 mmol) of (6-chloro-benzo[b]thiophen-2-ylmethyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine. The product was obtained as colorless liquid. MS (ISP) 370.0 (M+H)+.
Reference: [1] Patent: US2007/185113, 2007, A1, . Location in patent: Page/Page column 13
  • 3
  • [ 61072-56-8 ]
  • [ 2365-48-2 ]
  • [ 104795-85-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4793 - 4807
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6463 - 6466
[3] Patent: WO2016/100184, 2016, A1, . Location in patent: Paragraph 00268
  • 4
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 1301265-08-6 ]
  • [ 1322718-91-1 ]
  • [ 104795-85-9 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 11, p. 2868 - 2871
  • 5
  • [ 21211-18-7 ]
  • [ 104795-85-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 2003, vol. 68, # 5, p. 1020 - 1038
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