6-Chloro-1-benzothiophene-2-carboxylic acid → 4-{2-[(6-Chlorobenzo[b]thiophene-2-carbonyl)amino]-2-(2-chlorophenyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

HRID 32403

Reaction equation

HRID 32403 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][CH:17]([NH2:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:26][C:27]1[CH:28]=[CH:29][C:30]2[CH:34]=[C:33]([C:35](O)=[O:36])[S:32][C:31]=2[CH:38]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][CH2:16][CH:17]([NH:25][C:35]([C:33]2[S:32][C:31]3[CH:38]=[C:27]([Cl:26])[CH:28]=[CH:29][C:30]=3[CH:34]=2)=[O:36])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 71419196-Chloro-1-benzothiophene-2-carboxylic acidHCID 693096454-[2-Amino-2-(2-chlorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 693105624-{2-[(6-Chlorobenzo[b]thiophene-2-carbonyl)amino]-2-(2-chlorophenyl)ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Procedure

Using coupling method A, 4-[2-amino-2-(2-chlorophenyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester (300 mg, 0.8 mmol) and 6-chlorobenzo[b]thiophene-2-carboxylic acid (172 mg, 0.8 mmol) afforded, after purification (SiO2: 50% EtOAc in hexane), 353 mg (77%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 50% EtOAc in hexane), 353 mg (77%) of the title compound

Sources & evidence

ORD record
ord-d35e5ad97cae48f3be814ab7807cbfc6
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Linked notes

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