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 2089256Notes

Reaction equation

HRID 2089256 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>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]([CH3:41])([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

4

Reactant 2

HCID 6630Methyl benzenesulfonateHCID 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 162.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

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 (synthesised according to Example 7, step 1) (14.40 g, 26.25 mmol) and methyl benzenesulfonate (3.82 ml, 28.88 mmol) in acetone (127 ml) was heated at 55° C. for 18 h. The solvents were removed by rotary evaporation and the foam-like residue was suspended in a mixture of 2-propanol:ethanol (5:1) (100 mL) and heated to 80° C. and was then stirred at room temperature over night. The precipitate was filtered off, washed twice with a mixture of 2-propanol:ethanol (5:1) (2×20 mL), washed once with heptane (50 mL) and air dried to afford 16.94 g of a white powder. The solid was further dried at 55° C. in vacuum overnight to afford of the title compound (16.75 g, 88%) as an off-white solid; 1H NMR (400 MHz, dmso) δ 1.81 (3H, s), 1.90 (2H, m), 3.01 (9H, s), 3.27 (4H, m), 6.72 (1H, d), 7.30 (3H, m), 7.59 (2H, m), 7.67 (2H, d), 7.71 (1H, d), 7.85 (2H, m), 7.94 (4H, m), 8.04 (1H, s), 9.41 (1H, t); APCI-MS m/z: 563 [M+].

Workup

  1. customThe solvents were removed by rotary evaporation
  2. additionthe foam-like residue was suspended in a mixture of 2-propanol:ethanol (5:1) (100 mL)
  3. filtrationThe precipitate was filtered off
  4. washwashed twice with a mixture of 2-propanol:ethanol (5:1) (2×20 mL)
  5. washwashed once with heptane (50 mL) and air
  6. customdried

Sources & evidence

ORD record
ord-c2a03e53e9744650857e9220133deb63
Source dataset
uspto-grants-2013_05
Patent number
US08436024B2

Reaction notes

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