Methanesulfonyl chloride → HCID 59631559, compound

HRID 1431666Notes

Reaction equation

HRID 1431666 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:21][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:27]=1)=[C:5]([CH3:20])[C:6]([N:13]1[CH2:18][CH2:17][NH:16][C@@H:15]([CH3:19])[CH2:14]1)=[N:7]2.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4]([NH:21][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:27]=1)=[C:5]([CH3:20])[C:6]([N:13]1[CH2:18][CH2:17][N:16]([S:35]([CH3:34])(=[O:37])=[O:36])[C@@H:15]([CH3:19])[CH2:14]1)=[N:7]2

Participants

3

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59631072HCID 59631072, compound

Product 1

HCID 59631559HCID 59631559, compound

Procedure

Essentially prepared according to Procedure M using (S)-5,7-difluoro-3-methyl-2-(3-methylpiperazin-1-yl)-N-(5-morpholinopyridin-3-yl)quinolin-4-amine (50 mg, 0.11 mmol) and methylsulfonyl chloride to give (S)-5,7-difluoro-3-methyl-2-(3-methyl-4-(methylsulfonyl)piperazin-1-yl)-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (CDCl3) δ ppm 7.95 (1H, d, J=2.5 Hz), 7.66 (1H, d, J=2.3 Hz), 7.30 (1H, ddd, J=9.9, 2.5, 1.3 Hz), 6.92 (1H, d, J=13.3 Hz), 6.83 (1H, ddd, J=13.9, 8.7, 2.6 Hz), 6.60 (1H, t, J=2.3 Hz), 4.15-4.28 (1H, m), 3.86 (4H, dd, J=5.7, 4.1 Hz), 3.65-3.80 (2H, m), 3.58 (1H, dt, J=12.9, 1.9 Hz), 3.51 (1H, td, J=12.3, 2.9 Hz), 3.22 (1H, dd, J=12.9, 3.5 Hz), 3.13-3.19 (4H, m), 3.06 (1H, td, J=12.3, 3.2 Hz), 2.93 (3H, s), 2.09 (3H, s), 1.41 (3H, d, J=6.8 Hz). Mass Spectrum (ESI) m/e=533.2 (M+1).

Workup

  1. customEssentially prepared

Sources & evidence

ORD record
ord-b7dce7e8382b4233be2ade20a35aa948
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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