Diisopropylethylamine → 6-Chloro-2-(3,3-difluoropyrrolidin-1-yl)-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexylmethyl)-amide

HRID 1056723Notes

Reaction equation

HRID 1056723 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](Cl)=[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.CCN(C(C)C)C(C)C.[F:34][C:35]1([F:40])[CH2:39][CH2:38][NH:37][CH2:36]1>>[OH:1][C:2]1([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([N:37]4[CH2:38][CH2:39][C:35]([F:40])([F:34])[CH2:36]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

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27828273,3-DifluoropyrrolidineHCID 866233652,6-Dichloro-quinoline-5-carboxylic acid (1-hydroxy-3methyl-cyclohexylmethyl)-amide

Product 1

HCID 1185666306-Chloro-2-(3,3-difluoropyrrolidin-1-yl)-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexylmethyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 1 using 2,6-dichloro-quinoline-5-carboxylic acid (1-hydroxy-3methyl-cyclohexylmethyl)-amide, DIPEA and 3,3-difluoropyrrolidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.75 (1H), 7.85 (m, 1H), 7.58 (2H), 7.05 (1H), 4.16 (s, 1H), 3.89 (m, 2H), 3.70 (m, 1H), 3.55 (m, 1H), 3.26 (m, 2H), 2.44 (m, 2H), 2.06 (m, 2H), 1.85 (m, 2H), 1.74-1.76 (m, 5H), 1.27-1.32 (m, 1H), 0.83 (d, 3H). m/z: 438 [M+H]

Sources & evidence

ORD record
ord-3b214002be114ec3a9270c0d8bbe8fe6
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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