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

HRID 32410Notes

Reaction equation

HRID 32410 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][C@H:17]([NH2:22])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[C:32]2[C:27](=[CH:28][C:29]([C:33](O)=[O:34])=[CH:30][CH:31]=2)[NH:26][CH:25]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][CH2:16][C@H:17]([NH:22][C:33]([C:29]2[CH:28]=[C:27]3[C:32]([C:24]([Cl:23])=[CH:25][NH:26]3)=[CH:31][CH:30]=2)=[O:34])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 155430423-Chloro-1H-indole-6-carboxylic acidHCID 693096604-[(R)-2-Amino-2-(butyl)ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 693079004-{(R)-2-[(3-Chloro-1H-indole-6-carbonyl)amino]-2-(butyl)-ethoxymethyl}piperidine-1-carboxylic acid tert-butyl ester

Procedure

Using coupling method A, 4-[(R)-2-amino-2-(butyl)-ethoxymethyl]piperidine-1-carboxylic acid tert-butyl ester (195 mg, 0.62 mmol) and 3-chloroindole-6-carboxylic acid (133 mg, 0.68 mmol) afforded, after purification (SiO2: 40% EtOAc in hexane), 90 mg (29%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 40% EtOAc in hexane), 90 mg (29%) of the title compound

Sources & evidence

ORD record
ord-049c041b61f54e4ea5a022a8e7cf3e8d
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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