3-Chlorobenzo(b)thiophene-2-carbonyl chloride → tert-Butyl (4-{(3-chloro-benzo[b]thiophene-2-carbonyl)-[4-methoxy-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

HRID 2389571Notes

Reaction equation

HRID 2389571 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[CH2:21][NH:22][CH:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:25][CH2:24]1.[Cl:38][C:39]1[C:40]2[CH:50]=[CH:49][CH:48]=[CH:47][C:41]=2[S:42][C:43]=1[C:44](Cl)=[O:45]>>[Cl:38][C:39]1[C:40]2[CH:50]=[CH:49][CH:48]=[CH:47][C:41]=2[S:42][C:43]=1[C:44]([N:22]([CH2:21][C:4]1[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH:23]1[CH2:28][CH2:27][CH:26]([N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35])[CH2:25][CH2:24]1)=[O:45]

Participants

3

Reactant 2

HCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 59683508tert-Butyl (4-{[4-methoxy-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

Product 1

HCID 59683634tert-Butyl (4-{(3-chloro-benzo[b]thiophene-2-carbonyl)-[4-methoxy-4'-(2,2,2-trifluoro-acetyl)-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

Procedure

Biaryl amine 16 (467 mg, 0.90 mmol) is treated with 3-chlorobenzo-[b]thiophene-2-carbonyl chloride (290 mg, 1.26 mmol) using Method D to give the title compound.

Sources & evidence

ORD record
ord-46f563a0a6aa4a74bb6569006700599c
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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