3-Chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl chloride → tert-Butyl {4-[[5-(6-amino-pyridin-3-yl)-2-methoxy-benzyl]-(3-chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

HRID 2389640Notes

Reaction equation

HRID 2389640 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:31][CH3:32])=[C:12]([CH:30]=2)[CH2:13][NH:14][CH:15]2[CH2:20][CH2:19][CH:18]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]2)=[CH:4][CH:3]=1.[Cl:33][C:34]1[C:35]2[C:45]([F:46])=[CH:44][CH:43]=[C:42]([F:47])[C:36]=2[S:37][C:38]=1[C:39](Cl)=[O:40]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:31][CH3:32])=[C:12]([CH:30]=2)[CH2:13][N:14]([C:39]([C:38]2[S:37][C:36]3[C:42]([F:47])=[CH:43][CH:44]=[C:45]([F:46])[C:35]=3[C:34]=2[Cl:33])=[O:40])[CH:15]2[CH2:16][CH2:17][CH:18]([N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:19][CH2:20]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 219384153-Chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl chlorideHCID 59683549tert-Butyl {4-[5-(6-amino-pyridin-3-yl)-2-methoxy-benzylamino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 59683462tert-Butyl {4-[[5-(6-amino-pyridin-3-yl)-2-methoxy-benzyl]-(3-chloro-4,7-difluorobenzo[b]thiophene-2-carbonyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Crude biaryl amine 142 (300 mg, 0.68 mmol) is treated with acid chloride 8 (182 mg, 0.68 mmol) using Method D to give the title compound.

Sources & evidence

ORD record
ord-79399900346b4996a0f8799c9f6e0f04
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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