Methyl benzenesulfonate → 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamido)-N,N,N-trimethylpropan-1-aminium benzene sulfonate

HRID 2089257Notes

Reaction equation

HRID 2089257 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[C:16]([C:32]([NH:34][CH2:35][CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])=[O:33])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=4)[C:19]=3[CH3:20])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[C:41]1([S:47]([O:50]C)(=[O:49])=[O:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[CH3:52]C1CCCO1>CC(C)=O>[C:41]1([S:47]([O-:50])(=[O:49])=[O:48])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:15]=[C:16]([C:32]([NH:34][CH2:35][CH2:36][CH2:37][N+:38]([CH3:52])([CH3:40])[CH3:39])=[O:33])[C:17](=[O:31])[N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[CH:22]=4)[C:19]=3[CH3:20])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6630Methyl benzenesulfonateHCID 73012-MethyltetrahydrofuranHCID 582180475-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-N-(3-(dimethylamino)propyl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 866523733-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamido)-N,N,N-trimethylpropan-1-aminium benzene sulfonateYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-N-(3-(dimethylamino)propyl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamide (5 g, 9.12 mmol) and methyl benzenesulfonate (1.67 g, 9.52 mmol) in acetone (50 mL) was heated at 55° C. for 4 h. After cooling the reaction mixture to room temperature, 2-methyltetrahydrofuran (50 mL) was added. The resulting mixture was stirred overnight. The precipitate was filtered and dried in vacuum oven to give the title product as a light brown solid (6 g, 90%); 1H NMR (400 MHz, DMSO-d6) δ 9.35 (t, 1 H), 7.97 (s, 1 H), 7.83-7.94 (m, 4 H), 7.73-7.83 (m, 2 H), 7.64 (d, 1 H), 7.60 (d, 2 H), 7.46-7.56 (m, 2 H), 7.15-7.31 (m, 3 H), 6.65 (d, 1 H), 3.14-3.24 (m, 4 H), 2.94 (s, 9 H), 1.78-1.90 (m, 2 H), 1.75 (s, 3 H).

Workup

  1. filtrationThe precipitate was filtered
  2. customdried in vacuum oven

Sources & evidence

ORD record
ord-6d8285e22b1b4845a9557c52b5133c63
Source dataset
uspto-grants-2013_05
Patent number
US08436024B2

Reaction notes

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