2-Fluorobenzenesulphonyl chloride → HCID 59631588, compound

HRID 1431670Notes

Reaction equation

HRID 1431670 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:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40](Cl)(=[O:42])=[O:41]>>[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:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[F:33])(=[O:42])=[O:41])[CH2:17][CH2:18]1)=[N:7]2

Participants

3

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631588HCID 59631588, 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 2-fluorobenzene-1-sulfonyl chloride to give 5,7-difluoro-2-(4-(2-fluorophenylsulfonyl)-piperazin-1-yl)-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (DMSO-d6) δ ppm 2.00 (br s, 3H), 3.04 (t, J=4.4 Hz, 4H), 3.26 (br s, 4H), 3.33-3.37 (m, 4H), 3.68 (t, J=4.0 Hz, 4H), 6.48 (s, 1H), 7.14-7.19 (m, 1H), 7.26-7.29 (m, 1H), 7.45-7.54 (m, 3H), 7.77 (d, J=2.4 Hz, 2H), 7.81-7.85 (m, 1H), 8.35 (s, 1H). Mass Spectrum (ESI) m/e=599.4 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-163a52b2f56f4b3f9611a93b1c1df2e4
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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