6-Chloro-N,N-dimethylnicotinamide → 1-(4-Diethylaminophenyl)-5-(5-dimethylcarbamoylpyridin-2-yloxy)-2-ethoxycarbonylmethylindole-3-carboxylic acid ethyl ester

HRID 420947Notes

Reaction equation

HRID 420947 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2].Cl[C:34]1[CH:44]=[CH:43][C:37]([C:38]([N:40]([CH3:42])[CH3:41])=[O:39])=[CH:36][N:35]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:34]3[CH:44]=[CH:43][C:37]([C:38](=[O:39])[N:40]([CH3:41])[CH3:42])=[CH:36][N:35]=3)[CH:13]=2)[N:8]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 123642316-Chloro-N,N-dimethylnicotinamideHCID 666576271-(4-Diethylaminophenyl)-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester

Product 1

HCID 666576931-(4-Diethylaminophenyl)-5-(5-dimethylcarbamoylpyridin-2-yloxy)-2-ethoxycarbonylmethylindole-3-carboxylic acid ethyl ester

Procedure

The title compound was prepared in accordance with step (c) Example 38 from 1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester (120 mg, 0.28 mmol, see step (b) Example 1) and 6-chloro-N,N-dimethyl-nicotinamide (78 mg, 0.42 mmol). Yield 79 mg (48%).

Sources & evidence

ORD record
ord-3c21d2aa3d0740b1a4584c42a014f36a
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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