5-Chloro-1H-indole-2-carboxylic acid → 5-Chloro-N-[(R)-2-(1-isopropylpiperidine-4-ylmethoxy)-1-phenylethyl]-1H-indole-2-carboxamide hydrochloride

HRID 32449Notes

Reaction equation

HRID 32449 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][O:11][CH2:12][C@H:13]([NH2:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([C:31](O)=[O:32])=[CH:25]2>>[ClH:21].[Cl:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([C:31]([NH:20][C@H:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH2:12][O:11][CH2:10][CH:7]1[CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH2:9][CH2:8]1)=[O:32])=[CH:25]2

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 69309716HCID 69309716, compound

Product 1

HCID 693106025-Chloro-N-[(R)-2-(1-isopropylpiperidine-4-ylmethoxy)-1-phenylethyl]-1H-indole-2-carboxamide hydrochloride

Procedure

Using coupling method A, (R)-2-(1-isopropylpiperidin-4-ylmethoxy)-1-phenylethylamine (200 mg, 0.73 mmol) and 5-chloroindole-2-carboxylic acid (142 mg, 0.75 mmol) afforded, after purification (SiO2: 4:2:1 DCM:EtOAc:isopropylamine) and conversion to the HCl salt by general method A, 320 mg (92%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 4:2:1 DCM:EtOAc:isopropylamine) and conversion to the HCl salt by general method A, 320 mg (92%) of the title compound

Sources & evidence

ORD record
ord-ba18e4c1542448fcba388a7620aac548
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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