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

HRID 2389579Notes

Reaction equation

HRID 2389579 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[CH2:20][NH:21][CH:22]1[CH2:27][CH2:26][CH:25]([N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:24][CH2:23]1.[Cl:37][C:38]1[C:39]2[CH:49]=[CH:48][CH:47]=[CH:46][C:40]=2[S:41][C:42]=1[C:43](Cl)=[O:44]>>[Cl:37][C:38]1[C:39]2[CH:49]=[CH:48][CH:47]=[CH:46][C:40]=2[S:41][C:42]=1[C:43]([N:21]([CH2:20][C:4]1[CH:5]=[C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]([F:18])([F:17])[F:19])=[CH:13][CH:14]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH:22]1[CH2:27][CH2:26][CH:25]([N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:24][CH2:23]1)=[O:44]

Participants

3

Reactant 2

HCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 59683565tert-Butyl {4-[(4-methoxy-4'-trifluoromethoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Product 1

HCID 59683491tert-Butyl {4-[(3-chloro-benzo[b]thiophene-2-carbonyl)-(4-methoxy-4'-trifluoromethoxy-biphenyl-3-ylmethyl)-amino]-cyclohexyl}-methyl-carbamate

Procedure

Biaryl amine 31 (220 mg, 0.43 mmol) is treated with 3-chloro-benzo[b]thiophene-2-carbonyl chloride (120 mg, 0.52 mmol) using Method D to give the title compound.

Sources & evidence

ORD record
ord-da74260e7ae343d69cdbbe762c5e656c
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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