Pyridine-3-sulfonyl chloride → HCID 59631124, compound

HRID 1431674Notes

Reaction equation

HRID 1431674 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.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([S:39](Cl)(=[O:41])=[O:40])[CH:34]=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:39]([C:35]3[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=3)(=[O:41])=[O:40])[CH2:17][CH2:18]1)=[N:7]2

Participants

3

Reactant 2

HCID 3164136Pyridine-3-sulfonyl chlorideHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631124HCID 59631124, 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 pyridine-3-sulfonyl chloride to give 5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(4-(pyridin-3-ylsulfonyl)piperazin-1-yl)quinolin-4-amine. 1H NMR (DMSO-d6) δ ppm 1.98 (d, J=6.0 Hz, 3H), 3.04 (t, J=4.8 Hz, 4H), 3.18 (br s, 4H), 3.33-3.37 (m, 4H), 3.69 (t, J=4.4 Hz, 4H), 6.48 (s, 1H), 7.13-7.19 (m, 1H), 7.25-7.28 (m, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.70-7.77 (m, 1H), 7.77 (d, J=2.0 Hz, 1H,), 8.19-8.22 (m, 1H), 8.34 (s, 1H), 8.90-8.91 (m, 1H), 8.95 (d, J=2.4 Hz, 1H). Mass Spectrum (ESI) m/e=582.4 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2cdaf37cc81841dc8169c076103b2008
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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