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

HRID 2389590Notes

Reaction equation

HRID 2389590 reaction equation
[CH:1]([N:3]([CH3:35])[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:2].[Cl:36][C:37]1[C:38]2[CH:48]=[CH:47][CH:46]=[CH:45][C:39]=2[S:40][C:41]=1[C:42](Cl)=[O:43]>>[Cl:36][C:37]1[C:38]2[CH:48]=[CH:47][CH:46]=[CH:45][C:39]=2[S:40][C:41]=1[C:42]([N:19]([CH2:18][C:12]1[CH:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N:3]([CH:1]=[O:2])[CH3:35])=[CH:5][CH:6]=2)[CH:15]=[CH:14][C:13]=1[O:16][CH3:17])[CH:20]1[CH2:25][CH2:24][CH:23]([N:26]([CH3:34])[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:30])[CH3:31])[CH2:22][CH2:21]1)=[O:43]

Participants

3

Reactant 2

HCID 5198983-Chlorobenzo(b)thiophene-2-carbonyl chlorideHCID 25208192tert-Butyl (4-{[4'-(formyl-methyl-amino)-4-methoxy-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

Product 1

HCID 25208343tert-Butyl (4-{(3-chloro-benzo[b]thiophene-2-carbonyl)-[4'-(formyl-methyl-amino)-4-methoxy-biphenyl-3-ylmethyl]-amino}-cyclohexyl)-methyl-carbamate

Procedure

Biaryl amine 52 (325 mg, 0.64 mmol) is treated with 3-chloro-benzo[b]thiophene-2-carbonyl chloride (171 mg, 0.74 mmol) using Method D to give the title compound.

Sources & evidence

ORD record
ord-e4bf2533db21485297a3273a4a2ee3ae
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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