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

HRID 1056698Notes

Reaction equation

HRID 1056698 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.CC[N:27]([CH:31]([CH3:33])C)[CH:28]([CH3:30])C.N1CC[CH:36]([CH:39]([OH:41])C)C1>>[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:27]4[CH2:28][CH2:30][CH:33]([CH2:36][CH2:39][OH:41])[CH2:31]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 225601621-(Pyrrolidin-3-yl)ethan-1-olHCID 1185560912,6-Dichloro-quinoline-5-carboxylic acid (3,3-difluoro-cyclohexylmethyl)-amide

Product 1

HCID 1185665986-Chloro-2-(3-hydroxyethyl-pyrrolidin-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-ylethanol. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.72 (m, 1H), 7.75 (1H), 7.48 (2H), 6.96 (1H), 4.48 (1H), 3.79 (m, 1H), 3.66 (m, 1H), 3.49 (m, 2H), 3.34 (m, 1H), 3.23 (m, 2H), 3.09 (m, 1H), 2.44 (m, 1H), 2.12 (m, 1H), 2.06 (m, 2H), 1.85 (m, 2H), 1.77 (m, 2H), 1.60 (m, 4H), 1.27-1.30 (m, 2H). m/z: 452 [M+H]

Sources & evidence

ORD record
ord-df610e3a043b489a8332290e34fb48de
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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