Water → Benzenesulfonate 3-[({5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-1-yl}carbonyl)amino]-N,N,N-trimethylpropan-1-aminium

HRID 1480029Notes

Reaction equation

HRID 1480029 reaction equation
[C:1]1([S:7]([O:10]C)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[N:29]([C:30]([NH:32][CH2:33][CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])=[O:31])[C:28](=[O:39])[N:27]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=4)[C:26]=3[CH3:50])=[CH:23][CH:22]=[N:21]2)=[CH:16][CH:15]=1)#[N:13].O.CCOC(C)=O>C1COCC1>[C:12]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[C:24]([C:25]3[N:29]([C:30]([NH:32][CH2:33][CH2:34][CH2:35][N+:36]([CH3:1])([CH3:37])[CH3:38])=[O:31])[C:28](=[O:39])[N:27]([C:40]4[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:47])[F:48])[CH:41]=4)[C:26]=3[CH3:50])=[CH:23][CH:22]=[N:21]2)=[CH:16][CH:15]=1)#[N:13].[C:1]1([S:7]([O-:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6630Methyl benzenesulfonateHCID 8857Ethyl AcetateHCID 1213937355-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-N-[3-(dimethylamino)propyl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazole-1-carboxamide

Product 1

HCID 121393709Benzenesulfonate 3-[({5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-1-yl}carbonyl)amino]-N,N,N-trimethylpropan-1-aminiumYield 140.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl benzenesulfonate (0.019 mL, 0.14 mmol) was added to a solution of 5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-N-[3-(dimethylamino)propyl]-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazole-1-carboxamide (Example 9) (77 mg, 0.14 mmol) in THF (3.0 mL). The mixture was stirred for 2 hr then allowed to stand at RT for 2 days. Water (15 mL) and EtOAc (15 ml) were added with stirring. The phases were separated. The aqueous phase was washed with EtOAc (15 mL) then diluted with MeCN. The solvents were removed by lyophilisation to afford the title compound (70 mg) a white solid.

Workup

  1. waitto stand at RT for 2 days
  2. stirringwith stirring
  3. customThe phases were separated
  4. washThe aqueous phase was washed with EtOAc (15 mL)
  5. additionthen diluted with MeCN
  6. customThe solvents were removed by lyophilisation

Sources & evidence

ORD record
ord-f65d8d27850047059ca48995a8d1e035
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

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