Dimethylamine → 6-Chloro-2-(3-dimethylamino-cyclopentyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexyl methyl)-amide

HRID 1056794Notes

Reaction equation

HRID 1056794 reaction equation
[OH:1][C:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([CH:24]4[CH2:28][CH2:27][C:26](=O)[CH2:25]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH2:3]1.[CH3:30][NH:31][CH3:32]>>[OH:1][C:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([CH:24]4[CH2:28][CH2:27][CH:26]([N:31]([CH3:32])[CH3:30])[CH2:25]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])[CH2:7][CH2:6][CH2:5][CH:4]([CH3:8])[CH2:3]1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 1317364476-Chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexylmethyl)-amide

Product 1

HCID 1185666886-Chloro-2-(3-dimethylamino-cyclopentyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexyl methyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 133 using 6-chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (1-hydroxy-3-methylcyclohexyl methyl)-amide, and dimethylamine. 1H NMR (400 MHz, DMSO-d6) δ ppm (VTNMR: 80° C.): 8.26-8.24 (m, 1H), 8.11-8.09 (m, 1H), 7.97-7.94 (m, 1H), 7.73-7.70 (m, 1H), 7.56-7.54 (m, 1H), 3.87-3.85 (m, 1H), 3.46-3.33 (m, 3H), 2.77-2.49 (m, 1H), 2.25-1.34 (m, 20H), 0.87-0.77 (m, 1H). m/z: 444.0 [M+H]+

Sources & evidence

ORD record
ord-f397f249934e4003be1690018a82a01a
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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