3-Chloro-1H-indole-6-carboxylic acid → HCID 44444046, compound

HRID 32461Notes

Reaction equation

HRID 32461 reaction equation
Cl.Cl.[CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][N:13]([CH3:23])[CH2:14][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH2:16])[CH2:8][CH2:7]1)([CH3:5])[CH3:4].[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>>[Cl:24][C:25]1[C:33]2[C:28](=[CH:29][C:30]([C:34]([NH:16][C@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:14][N:13]([CH2:12][CH:9]3[CH2:8][CH2:7][N:6]([CH:3]([CH3:5])[CH3:4])[CH2:11][CH2:10]3)[CH3:23])=[O:35])=[CH:31][CH:32]=2)[NH:27][CH:26]=1

Participants

3

Reactant 2

HCID 155430423-Chloro-1H-indole-6-carboxylic acidHCID 69313099HCID 69313099, compound

Product 1

HCID 44444046HCID 44444046, compound

Procedure

Using coupling method A, crude (R)-N2-(1-isopropyl-piperidin-4-ylmethyl)-N2-methyl-1-phenylethane-1,2-diamine dihydrochloride (500 mg, 1.4 mmol) and 3-chloroindole-6-carboxylic acid (325 mg, 1.7 mmol) afforded, after purification (SiO2: 0 to 30% isopropylamine in 1:1 hexane:EtOAc), 115 mg (18%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 0 to 30% isopropylamine in 1:1 hexane:EtOAc), 115 mg (18%) of the title compound

Sources & evidence

ORD record
ord-923545ba89784e14b2b80e305dfdf2e3
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

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