5-Chloro-1H-indole-2-carboxylic acid → 5-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide

HRID 1376146Notes

Reaction equation

HRID 1376146 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:12][CH:13]2[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15][CH2:14]2)[C:3]1=[O:21].[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27]([C:32](O)=[O:33])=[CH:26]2>>[Cl:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27]([C:32]([NH:1][CH:2]1[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]([CH2:12][CH:13]3[CH2:14][O:15][C:16]([CH3:19])([CH3:20])[O:17][CH2:18]3)[C:3]1=[O:21])=[O:33])=[CH:26]2

Participants

3

Reactant 2

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 219068303-amino-1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 102386835-Chloro-N-{1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamideYield 85%

Procedure

Following a standard amide coupling procedure analogous to Example 1, using 3-amino-1-[(2,2-dimethyl-1,3-dioxan-5-yl)methyl]-3,4-dihydroquinolin-2(1H)-one (Method 4) as the amine and 5-chloroindole-2-carboxylic acid as the acid afforded the title compound (85%) as a white solid.

Sources & evidence

ORD record
ord-f8ac9c01171d4641bf8786b419cbc18f
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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