1-(2-(6-(4-oxazol-5-yl-phenoxy)-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone → 1-(2-(6-(4-oxazol-5-yl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

HRID 13268Notes

Reaction equation

HRID 13268 reaction equation
[O:1]1[C:5]([C:6]2[CH:43]=[CH:42][C:9]([O:10][C:11]3[C:12]([CH:34]4[CH2:38][CH2:37][CH2:36][N:35]4[C:39](=[O:41])[CH3:40])=[CH:13][C:14]4[N:18](COCC[Si](C)(C)C)[C:17]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=5)=[N:16][C:15]=4[CH:33]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1>FC(F)(F)C(O)=O>[O:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([O:10][C:11]3[C:12]([CH:34]4[CH2:38][CH2:37][CH2:36][N:35]4[C:39](=[O:41])[CH3:40])=[CH:13][C:14]4[NH:18][C:17]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=5)=[N:16][C:15]=4[CH:33]=3)=[CH:42][CH:43]=2)=[CH:4][N:3]=[CH:2]1

Participants

3

Reactant 1

HCID 231453191-(2-(6-(4-oxazol-5-yl-phenoxy)-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Product 1

HCID 231451671-(2-(6-(4-oxazol-5-yl-phenoxy)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

24 mg of 1-(2-(6-(4-oxazol-5-yl-phenoxy)-2-pyridin-2-yl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone was dissolved in 1 ml of trifluoroacetic acid, and the reaction liquid was stirred at room temperature for 2 hours. The 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) to obtain the entitled compound as a yellow oily substance.

Workup

  1. customthe reaction liquid
  2. customThe 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. customto obtain the entitled compound as a yellow oily substance

Sources & evidence

ORD record
ord-885ece449c4e46bd9278f8c3a933ff3d
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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