Dimethylamine → 2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidine-1-carboxylic acid dimethylamide

HRID 13352Notes

Reaction equation

HRID 13352 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][S:5]([C:8]1[CH:46]=[CH:45][C:11]([O:12][C:13]2[C:14]([CH:28]3[CH2:32][CH2:31][CH2:30][N:29]3[C:33]([O:35]C3C=CC([N+]([O-])=O)=CC=3)=O)=[CH:15][C:16]3[NH:20][CH:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[NH:18][C:17]=3[CH:27]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6]>O1CCCC1>[CH3:1][N:2]([CH3:3])[C:33]([N:29]1[CH2:30][CH2:31][CH2:32][CH:28]1[C:14]1[C:13]([O:12][C:11]2[CH:10]=[CH:9][C:8]([S:5]([CH3:4])(=[O:6])=[O:7])=[CH:46][CH:45]=2)=[CH:27][C:17]2[N:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[NH:20][C:16]=2[CH:15]=1)=[O:35]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 231457624-nitrophenyl 2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-5-yl)-pyrrolidin-1-carboxylate

Product 1

HCID 674828792-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidine-1-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

1 ml of dimethylamine (2.0 M tetrahydrofuran solution) was added to a tetrahydrofuran (1 ml) solution of 20 mg of 4-nitrophenyl 2-(6-(4-methanesulfonyl-phenoxy)-2-pyridin-2-yl-2,3-dihydro-1H-benzimidazol-5-yl)-pyrrolidin-1-carboxylate, and the reaction liquid was stirred overnight in a sealed tube at 100° C. The reaction solvent was evaporated away under reduced pressure, and the resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was diluted with ethyl acetate, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound as a white solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction solvent was evaporated away under reduced pressure
  3. customthe resulting residue was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  4. additionThe solvent of the resulting fraction was diluted with ethyl acetate
  5. washwashed with aqueous saturated sodium bicarbonate
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-8f82ee6fd6fd46ec8c851cfe518bef92
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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