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

HRID 1056695Notes

Reaction equation

HRID 1056695 reaction equation
[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH2:5][C:4]([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])[CH2:3]1.CCN(C(C)C)C(C)C.[F:35][C:36]1([F:40])[CH2:39][NH:38][CH2:37]1>>[F:1][C:2]1([F:25])[CH2:7][CH2:6][CH2:5][C:4]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([N:38]4[CH2:39][C:36]([F:40])([F:35])[CH2:37]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:3]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27582483,3-DifluoroazetidineHCID 1185560332,6-Dichloro-quinoline-5-carboxylic acid (3,3-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185666146-Chloro-2-(3,3-difluoroazetidin-1-yl)-quinoline-5-carboxylic acid (3,3-difluoro-1-hydroxycyclohexylmethyl)-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-1-hydroxycyclohexylmethyl)-amide, DIPEA and 3,3-difluoroazetidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.75 (1H), 7.94 (m, 1H), 7.66 (2H), 7.05 (1H), 4.57 (m, 4H), 3.49 (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: 446 [M+H]

Sources & evidence

ORD record
ord-a615a5434fef441485d32340725243b8
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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