Ethanesulfonyl chloride → HCID 59631464, compound

HRID 1431673Notes

Reaction equation

HRID 1431673 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.[CH2:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34]>>[CH2:33]([S:35]([N:16]1[CH2:15][CH2:14][N:13]([C:6]2[C:5]([CH3:19])=[C:4]([NH:20][C:21]3[CH:22]=[N:23][CH:24]=[C:25]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[CH:26]=3)[C:3]3[C:8](=[CH:9][C:10]([F:12])=[CH:11][C:2]=3[F:1])[N:7]=2)[CH2:18][CH2:17]1)(=[O:37])=[O:36])[CH3:34]

Participants

3

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 596310285,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)-2-(piperazin-1-yl)quinolin-4-amine

Product 1

HCID 59631464HCID 59631464, 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 ethylsulfonyl chloride to give 2-(4-(ethylsulfonyl)piperazin-1-yl)-5,7-difluoro-3-methyl-N-(5-morpholinopyridin-3-yl)quinolin-4-amine. 1H NMR (DMSO-d6) δ ppm 1.15 (t, J=7.2 Hz, 3H), 2.08 (s, 3H), 3.05-3.11 (br s, 4H), 3.13 (q, J=7.2 Hz, 2H), 3.33 (br s, 8H), 3.69 (m, 4H), 6.51 (br s, 1H), 7.10-7.15 (m, 1H), 7.28-7.31 (m, 1H), 7.46 (s, 1H), 7.74 (s, 1H), 8.39 (s, 1H). Mass Spectrum (ESI) m/e=533.4 (M+1).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3f2928f9a61d4e25b73b3f429ef3f501
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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