3-Fluorobenzenesulfonyl Chloride → HCID 59631444, compound

HRID 1431671Notes

Reaction equation

HRID 1431671 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.[F:33][C:34]1[CH:35]=[C:36]([S:40](Cl)(=[O:42])=[O:41])[CH:37]=[CH:38][CH:39]=1>>[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[CH2:14][CH2:15][N:16]([S:40]([C:36]3[CH:37]=[CH:38][CH:39]=[C:34]([F:33])[CH:35]=3)(=[O:42])=[O:41])[CH2:17][CH2:18]1)=[N:7]2

Participants

3

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631444HCID 59631444, 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 mg, 0.11 mmol) and 3-fluorobenzene-1-sulfonyl chloride to give 5,7-difluoro-2-(4-(3-fluorophenylsulfonyl)-piperazin-1-yl)-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (DMSO-d6) δ ppm 1.96 (br s, 3H), 3.03 (t, J=4.4 Hz, 4H), 3.14 (br s, 4H), 3.34-3.36 (m, 4H), 3.68 (t, J=4.4 Hz, 4H), 6.47 (s, 1H), 7.13-7.19 (m, 1H), 7.25-7.28 (m, 1H), 7.49 (d, J=2.0 Hz, 1H), 7.60-7.65 (m, 3H), 7.71-7.77 (m, 2H,), 8.36 (s, 1H). Mass Spectrum (ESI) m/e=599.4 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-341c460e3ebb4627ad028c59508055ab
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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