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

HRID 1056725Notes

Reaction equation

HRID 1056725 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][C@H: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][C@H:4]([CH3:8])[CH2:3]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27828273,3-DifluoropyrrolidineHCID 866233642,6-Dichloro-N-{[(1S,3S)-1-hydroxy-3-methylcyclohexyl]methyl}quinoline-5-carboxamide

Product 1

HCID 1185666196-Chloro-2-(3,3-difluoro-pyrrolidin-1-yl)-quinoline-5-carboxylic acid ((1S,3S)-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 ((1S,3S)-1-hydroxy-3-methyl-cyclohexylmethyl)-amide, DIPEA and 3,3-difluoropyrrolidine. 1H NMR (400 MHz, DMSO-d6): δ 8.54 (t, J=6.01 Hz, 1H), 7.89 (d, J=9.32 Hz, 1H), 7.54-7.61 (m, 2H), 7.04 (d, J=9.21 Hz, 1H), 4.16 (s, 1H), 3.96-4.03 (m, 2H), 3.45 (t, J=5.00 Hz, 2H), 3.27-3.28 (m, 2H), 2.56-2.59 (m, 3H), 1.73-1.75 (m, 1H), 1.52-1.61 (m, 4H), 1.46-1.47 (m, 1H), 1.34-1.38 (m, 1H), 1.18-1.19 (m, 1H), 0.84-0.87 (m, 4H). m/z: 438.2 [M+H]+

Sources & evidence

ORD record
ord-d08ef0a65d8b4dce88a728ddfb68a72e
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

Loading…