Diisopropylethylamine → 6-Chloro-2-(3-hydroxymethylpyrrolidin-1-yl)-quinoline-5-carboxylic acid (3,3-difluoro-cyclohexylmethyl)-amide

HRID 1056697Notes

Reaction equation

HRID 1056697 reaction equation
[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16](Cl)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:3]1.CCN(C(C)C)C(C)C.[NH:34]1[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35]1>>[F:1][C:2]1([F:24])[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([N:34]4[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:3]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 13400657(Pyrrolidin-3-yl)methanolHCID 1185560912,6-Dichloro-quinoline-5-carboxylic acid (3,3-difluoro-cyclohexylmethyl)-amide

Product 1

HCID 1185665946-Chloro-2-(3-hydroxymethylpyrrolidin-1-yl)-quinoline-5-carboxylic acid (3,3-difluoro-cyclohexylmethyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 1 using 2,6-dichloro-quinoline-5-carboxylic acid (3,3-difluoro-cyclohexylmethyl)-amide, DIPEA and pyrrolidin-3-ylmethanol. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72 (1H), 7.75 (m, 1H), 7.55 (2H), 7.05 (1H), 4.73 (1H), 3.65 (m, 2H), 3.50 (m, 3H), 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, 2H). m/z: 438 [M+H]

Sources & evidence

ORD record
ord-ddc704bf7e5344beb349eb9c78e48eac
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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