3-Chlorobenzo(b)thiophene-2-carbonyl chloride → 3-Chloro-benzo[b]thiophene-2-carboxylic acid [2-methoxy-5-(2-methyl-pyridin-4-yl)-benzyl]-(4-methylamino-cyclohexyl)-amide dihydrochloride

HRID 2389612Notes

Reaction equation

HRID 2389612 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=2)=[CH:22][C:4]=1[CH2:5][NH:6][CH:7]1[CH2:12][CH2:11][CH:10]([N:13]([CH3:21])C(=O)OC(C)(C)C)[CH2:9][CH2:8]1.[Cl:33][C:34]1[C:35]2[CH:45]=[CH:44][CH:43]=[CH:42][C:36]=2[S:37][C:38]=1[C:39](Cl)=[O:40]>>[ClH:33].[ClH:33].[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([CH3:32])[CH:27]=2)=[CH:22][C:4]=1[CH2:5][N:6]([CH:7]1[CH2:12][CH2:11][CH:10]([NH:13][CH3:21])[CH2:9][CH2:8]1)[C:39]([C:38]1[S:37][C:36]2[CH:42]=[CH:43][CH:44]=[CH:45][C:35]=2[C:34]=1[Cl:33])=[O:40]

Participants

3

Reactant 2

HCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 59683623tert-Butyl {4-[2-methoxy-5-(2-methyl-pyridin-4-yl)-benzylamino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 683138533-Chloro-benzo[b]thiophene-2-carboxylic acid [2-methoxy-5-(2-methyl-pyridin-4-yl)-benzyl]-(4-methylamino-cyclohexyl)-amide dihydrochlorideYield 123.5%

Procedure

Biaryl amine 88 (250 mg, 0.57 mmol) is treated with 3-chlorobenzo-[b]thiophene-2-carbonyl chloride (157 mg, 0.68 mmol) using Method D. The resultant amide (175 mg, 0.28 mmol) isolated after chromatography is then directly deprotected using Method F to afford the title compound.

Sources & evidence

ORD record
ord-edf558bbd027467fb73c6303a21f1f71
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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