Azetidine hydrochloride → 2-(3-Azetidin-1-yl-cyclopentyl)-6-chloro-quinoline-5-carboxylic acid (4,4-difluoro cyclohexylmethyl)-amide

HRID 1056789Notes

Reaction equation

HRID 1056789 reaction equation
[F:1][C:2]1([F:29])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:27][CH2:26][C:25](=O)[CH2:24]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1.Cl.[NH:31]1[CH2:34][CH2:33][CH2:32]1>>[F:1][C:2]1([F:29])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[CH:15][C:16]([CH:23]4[CH2:27][CH2:26][CH:25]([N:31]5[CH2:34][CH2:33][CH2:32]5)[CH2:24]4)=[N:17][C:18]=3[CH:19]=[CH:20][C:21]=2[Cl:22])=[O:11])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 12308726Azetidine hydrochlorideHCID 1185696266-Chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide

Product 1

HCID 1185666962-(3-Azetidin-1-yl-cyclopentyl)-6-chloro-quinoline-5-carboxylic acid (4,4-difluoro cyclohexylmethyl)-amide

Procedure

The title compound was synthesized according to the procedure described in example 133 using 6-chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-cyclohexylmethyl)-amide, and azetidine hydrochloride. 1H NMR (400 MHz, DMSO-d6): δ 10.08 (m, 1H), 8.81 (t, J=4.41 Hz, 1H), 8.06-8.03 (m, 1H), 8.00-7.96 (m, 1H), 7.81-7.77 (m, 1H), 7.62-7.58 (m, 1H), 4.17-4.06 (m, 5H), 4.06-4.04 (m, 1H), 3.29-3.26 (m, 2H), 2.50-2.44 (m, 5H), 2.07-2.03 (m, 3H), 1.90-1.84 (m, 7H), 1.78-1.74 (m, 1H), 1.31-1.27 (m, 2H). m/z: 462.3 [M+H]+

Sources & evidence

ORD record
ord-e9550c88f7ba478ba4224c6723f39a66
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

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