3,3-Difluoropyrrolidine → 6-Chloro-2-(3,3-difluoro-pyrrolidin-1-yl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

HRID 1056718Notes

Reaction equation

HRID 1056718 reaction equation
[F:1][C:2]1([F:25])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17](Cl)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH2:3]1.[F:26][C:27]1([F:32])[CH2:31][CH2:30][NH:29][CH2:28]1>>[F:1][C:2]1([F:25])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([N:29]4[CH2:30][CH2:31][C:27]([F:32])([F:26])[CH2:28]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 27828273,3-DifluoropyrrolidineHCID 1185560922,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185666246-Chloro-2-(3,3-difluoro-pyrrolidin-1-yl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 1 using 2,6-Dichloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclo hexyl methyl)-amide, and 3,3-Difluoro-pyrrolidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68-8.71 (bs, 1H), 7.89 (d, J=9.2 Hz, 1H), 7.55-7.62 (m, 2H), 7.03 (d, J=9.3 Hz, 1H), 4.67 (s, 1H), 3.96-4.03 (m, 2H), 3.76-3.80 (m, 2H), 3.37-3.39 (m, 2H), 2.54-2.61 (m, 2H), 1.88-2.08 (m, 4H), 1.68-1.76 (m, 4H). m/z: 460.2 [M+H]+

Sources & evidence

ORD record
ord-e480c1f9ddd14a6fb2040a4c144a7d79
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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