Trifluoroacetic acid → HCID 66755470, compound

HRID 1631998Notes

Reaction equation

HRID 1631998 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:45])[CH:15]([N:22]2[C:26]3[CH:27]=[C:28]([C:31]#[N:32])[CH:29]=[CH:30][C:25]=3[N:24]([S:33]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[C:23]2=[O:44])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:45])[CH:15]([N:22]2[C:26]3[CH:27]=[C:28]([C:31]#[N:32])[CH:29]=[CH:30][C:25]=3[N:24]([S:33]([C:36]3[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=3)(=[O:34])=[O:35])[C:23]2=[O:44])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66754949HCID 66754949, compound

Product 1

HCID 66755470HCID 66755470, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1-{2-[6-cyano-3-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydrobenzoimidazol-1-yl]-2-phenyl-acetyl}piperidin-4-yl)-carbamic acid tert-butyl ester (254 mg, 0.39 mmol) in CH2Cl2 (5 mL) was treated with trifluoroacetic acid (5 mL). The reaction mixture was stirred at room temperature for 2 hours, concentrated in vacuo and co-evaporated the solvent with toluene (3×). The residue was dissolved in CH2Cl2 (30 mL) and treated with solid K2CO3. The reaction mixture was stirred at room temperature for 1 hour, filtered and concentrated in vacuo to afford 3-[2-(4-amino-piperidin-1-yl)-2-oxo-1-phenyl-ethyl]-1-(4-methoxy-benzenesulfonyl)-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbonitrile (179 mg, 83%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (30 mL)
  3. additiontreated with solid K2CO3
  4. stirringThe reaction mixture was stirred at room temperature for 1 hour
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa72dba41d6a41a38651bef51132f8af
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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