Azetidine → 2-(Azetidin-1-yl)-6-chloro-quinoline-5-carboxylic acid (3,3-difluoro-1-hydroxycyclohexylmethyl)-amide

HRID 1056696Notes

Reaction equation

HRID 1056696 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.CC[N:28]([CH:32]([CH3:34])C)[CH:29](C)C.N1CCC1>>[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:28]4[CH2:29][CH2:34][CH2:32]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 10422AzetidineHCID 81531DiisopropylethylamineHCID 1185560332,6-Dichloro-quinoline-5-carboxylic acid (3,3-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185665742-(Azetidin-1-yl)-6-chloro-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 azetidine. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.75 (1H), 7.84 (m, 1H), 7.56 (2H), 6.85 (1H), 4.57 (m, 1H), 4.11 (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: 410 [M+H]

Sources & evidence

ORD record
ord-0e52fa2fbf6a451fbd09e211ec0ffb96
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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