3-Chloro-1H-indole-6-carboxylic acid → 4-{2-[(3-Chloro-1H-indole-6-carbonyl)amino]-2-cyclopentyl-ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

HRID 32409Notes

Reaction equation

HRID 32409 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]([NH2:23])[CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:24][C:25]1[C:33]2[C:28](=[CH:29][C:30]([C:34](O)=[O:35])=[CH:31][CH:32]=2)[NH:27][CH:26]=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:23][C:34]([C:30]2[CH:29]=[C:28]3[C:33]([C:25]([Cl:24])=[CH:26][NH:27]3)=[CH:32][CH:31]=2)=[O:35])[CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 155430423-Chloro-1H-indole-6-carboxylic acidHCID 693130454-(2-Amino-2-cyclopentyl-ethoxymethyl)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 693078664-{2-[(3-Chloro-1H-indole-6-carbonyl)amino]-2-cyclopentyl-ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Procedure

Using coupling method A, 4-(2-amino-2-cyclopentyl-ethoxymethyl)piperidine-1-carboxylic acid tert-butyl ester (460 mg, 1.4 mmol) and 3-chloroindole-6-carboxylic acid (275 mg, 1.4 mmol) afforded, after purification (SiO2: 40% EtOAc in hexane), 211 mg (30%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 40% EtOAc in hexane), 211 mg (30%) of the title compound

Sources & evidence

ORD record
ord-1ad637322827475abe3124466e52e92f
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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