3-Chloro-4-fluoro-1-benzothiophene-2-carbonyl chloride → tert-Butyl {4-[(4'-carbamoyl-4-methoxy-biphenyl-3-ylmethyl)-(3-chloro-4-fluoro-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389633Notes

Reaction equation

HRID 2389633 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH2:18][NH:19][CH:20]3[CH2:25][CH2:24][CH:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]3)[CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[Cl:35][C:36]1[C:37]2[C:47]([F:48])=[CH:46][CH:45]=[CH:44][C:38]=2[S:39][C:40]=1[C:41](Cl)=[O:42]>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH2:18][N:19]([C:41]([C:40]3[S:39][C:38]4[CH:44]=[CH:45][CH:46]=[C:47]([F:48])[C:37]=4[C:36]=3[Cl:35])=[O:42])[CH:20]3[CH2:25][CH2:24][CH:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:22][CH2:21]3)[CH:11]=2)=[CH:8][CH:9]=1)(=[O:3])[NH2:2]

Participants

3

Reactant 2

HCID 125946453-Chloro-4-fluoro-1-benzothiophene-2-carbonyl chlorideHCID 59683480tert-Butyl {4-[(4'-carbamoyl-4-methoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 59683612tert-Butyl {4-[(4'-carbamoyl-4-methoxy-biphenyl-3-ylmethyl)-(3-chloro-4-fluoro-benzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Biaryl amine 55 (216 mg, 0.46 mmol) is treated with acid chloride 6 (137 mg, 0.55 mmol) using Method D to give the title compound.

Sources & evidence

ORD record
ord-4b660e001eb4483db0ab04e9614c9b08
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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