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

HRID 1056799Notes

Reaction equation

HRID 1056799 reaction equation
[F:1][C:2]1([F:30])[CH2:7][CH2:6][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([CH:24]4[CH2:28][CH2:27][C:26](=O)[CH2:25]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:4][CH2:3]1.Cl.[NH:32]1[CH2:35][CH2:34][CH2:33]1>C(O)(=O)C>[F:1][C:2]1([F:30])[CH2:3][CH2:4][C:5]([CH2:9][NH:10][C:11]([C:13]2[C:14]3[CH:15]=[CH:16][C:17]([CH:24]4[CH2:28][CH2:27][CH:26]([N:32]5[CH2:35][CH2:34][CH2:33]5)[CH2:25]4)=[N:18][C:19]=3[CH:20]=[CH:21][C:22]=2[Cl:23])=[O:12])([OH:8])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 12308726Azetidine hydrochlorideHCID 1185666266-Chloro-2-(3-oxo-cyclopentyl)-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Product 1

HCID 1185666922-(3-Azetidin-1-yl-cyclopentyl)-6-chloro-quinoline-5-carboxylic acid (4,4-difluoro-1-hydroxy-cyclohexylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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-1-hydroxycyclohexyl methyl)-amide, and azetidine hydrochloride in glacial acetic acid. 1H NMR (400 MHz, DMSO-d6): δ 8.76 (t, J=6.0 Hz, 1H), 8.11-8.06 (m, 1H), 7.97-7.94 (m, 1H), 7.76-7.73 (m, 1H), 7.64-7.54 (m, 1H), 4.71 (s, 1H), 3.47-3.16 (m, 1H), 3.07-2.49 (m, 4H), 2.23-2.02 (m, 1H), 2.01-1.95 (m, 6H), 1.90 (s, 6H), 1.64-1.59 (m, 8H. m/z: 478.3 [M+H]+

Sources & evidence

ORD record
ord-fba9e51bd1a945a8ac7999d005eddcd7
Source dataset
uspto-grants-2016_07
Patent number
US09399623B2

Reaction notes

Loading…