Cyclopentanesulfonyl chloride → HCID 59631027, compound

HRID 1431682Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:26]=1)=[C:5]([CH3:19])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[N:7]2.[CH:33]1([S:38](Cl)(=[O:40])=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:33]1([S:38]([N:16]2[CH2:15][CH2:14][N:13]([C:6]3[C:5]([CH3:19])=[C:4]([NH:20][C:21]4[CH:22]=[N:23][CH:24]=[C:25]([N:27]5[CH2:32][CH2:31][O:30][CH2:29][CH2:28]5)[CH:26]=4)[C:3]4[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=4[F:1])[N:7]=3)[CH2:18][CH2:17]2)(=[O:40])=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

Reactant 2

HCID 3717197Cyclopentanesulfonyl chloride

HCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631027HCID 59631027, compound

Procedure

Prepared according to Procedure M using 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine (50.0 mg, 0.11 mmol) and cyclopentylsulfonyl chloride to give 2-(4-(cyclopentylsulfonyl)piperazin-1-yl)-5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 1.54-1.58 (m, 2H), 1.67 (s, 2H), 1.80-1.85 (m, 2H), 1.96-1.99 (m, 2H), 2.08 (s, 3H), 3.05 (t, J=4.4 Hz, 4H), 3.33 (s, 4H), 3.39 (t, J=4.8 Hz, 4H), 3.69 (t, J=3.6 Hz, 5H), 6.51 (s, 1H), 7.15-7.20 (m, 1H), 7.30 (d, J=11.2 Hz, 1H), 7.52 (s, 1H), 7.78 (s, 1H), 8.37 (s, 1H). Mass Spectrum (ESI) m/e=573.1 (M+1).

Workup

customPrepared

Sources & evidence

ORD record: ord-4083911a4ade48f590a30a9334f2d890
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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