Dimethylamine → 6-Chloro-2-(3-dimethylaminocyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexyl methyl)-amide

HRID 1056798Notes

Reaction equation

HRID 1056798 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][C:5]([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])([OH:8])[CH2:4][CH2:3]1.[CH3:31][NH:32][CH3:33]>>[F:30][C:2]1([F:1])[CH2:3][CH2:4][C:5]([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:32]([CH3:33])[CH3:31])[CH2:25]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 1185666266-Chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185666936-Chloro-2-(3-dimethylaminocyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-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 (4,4-difluoro-1-hydroxycyclohexyl methyl)-amide, and dimethylamine. 1H NMR (400 MHz, DMSO-d6): δ 8.76 (d, J=6.2 Hz, 1H), 8.13 (t, J=5.6 Hz, 1H), 8.11-7.96 (m, 1H), 7.79-7.77 (m, 2H), 7.59 (d, J=8.6 Hz, 1H), 3.41-2.85 (m, 1H), 2.84-2.50 (m, 1H), 2.50-2.49 (m, 2H), 2.48-2.46 (m, 6H), 2.25-2.07 (m, 1H), 2.01-1.91 (m, 4H), 1.90-1.85 (m, 5H), 1.73-1.69 (m, 4H). m/z: 466.3 [M+H]+

Sources & evidence

ORD record
ord-f60f6e1612f8400a8e973882433b6d67
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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