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

HRID 2389609Notes

Reaction equation

HRID 2389609 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[C:11]([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:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[Cl:35][C:36]1[C:37]2[CH:47]=[CH:46][CH:45]=[CH:44][C:38]=2[S:39][C:40]=1[C:41](Cl)=[O:42]>>[Cl:35][C:36]1[C:37]2[CH:47]=[CH:46][CH:45]=[CH:44][C:38]=2[S:39][C:40]=1[C:41]([N:19]([CH2:18][C:11]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH2:16][CH3:17])[CH:20]1[CH2:25][CH2:24][CH:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH2:22][CH2:21]1)=[O:42]

Participants

3

Reactant 2

HCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 59683463tert-Butyl {4-[(3'-cyano-4-ethoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 59683617tert-Butyl {4-[(3-chloro-benzo[b]thiophene-2-carbonyl)-(3'-cyano-4-ethoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Biaryl amine 81 (390 mg, 0.84 mmol) is treated with 3-chlorobenzo-[b]thiophene-2-carbonyl chloride (233 mg, 1.01 mmol) using Method D to give the title compound.

Sources & evidence

ORD record
ord-510e8733a38448dbb7be959566a9ee77
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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