3-Chloro-1H-indole-6-carboxylic acid → N-[(R)-2-(3-Chloro-1H-indole-6-carbonyl)amino-2-phenyl-ethyl]-N-(1-isopropylpiperidin-4-ylmethyl)carbamic acid 9H-fluoren-9-ylmethyl ester

HRID 32465Notes

Reaction equation

HRID 32465 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:37])[N:17]([CH2:28][C@H:29]([NH2:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl:38][C:39]1[C:47]2[C:42](=[CH:43][C:44]([C:48](O)=[O:49])=[CH:45][CH:46]=2)[NH:41][CH:40]=1>>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:37])[N:17]([CH2:28][C@H:29]([NH:36][C:48]([C:44]3[CH:43]=[C:42]4[C:47]([C:39]([Cl:38])=[CH:40][NH:41]4)=[CH:46][CH:45]=3)=[O:49])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([CH:25]([CH3:27])[CH3:26])[CH2:21][CH2:20]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 155430423-Chloro-1H-indole-6-carboxylic acidHCID 69310705N-[(R)-2-amino-2-phenyl-ethyl]-N-(1-isopropylpiperidin-4-ylmethyl)carbamic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 69307958N-[(R)-2-(3-Chloro-1H-indole-6-carbonyl)amino-2-phenyl-ethyl]-N-(1-isopropylpiperidin-4-ylmethyl)carbamic acid 9H-fluoren-9-ylmethyl ester

Procedure

Using coupling method A, crude N-[(R)-2-amino-2-phenyl-ethyl]-N-(1-isopropylpiperidin-4-ylmethyl)carbamic acid 9H-fluoren-9-ylmethyl ester (980 mg, 2.0 mmol) and 3-chloro-indole-6-carboxylic acid (462 mg, 2.4 mmol) afforded, after purification (SiO2: 0 to 30% isopropylamine in 1:1 hexane:EtOAc), 300 mg (23%) of the title compound.

Workup

  1. customafforded
  2. customafter purification (SiO2: 0 to 30% isopropylamine in 1:1 hexane:EtOAc), 300 mg (23%) of the title compound

Sources & evidence

ORD record
ord-376b01dfc6944e1d97570c003f0319c0
Source dataset
uspto-grants-2008_09
Patent number
US07427632B2

Reaction notes

Loading…