HCID 178514700, compound → HCID 178514701, compound

HRID 552593Notes

Reaction equation

HRID 552593 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[CH:9]=[CH:10]/[C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[S:26]([NH2:29])(=[O:28])=[O:27])=[CH:19][C:13]=2[N:12]=1>[Pd].CO>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[S:26]([NH2:29])(=[O:27])=[O:28])=[CH:19][C:13]=2[N:12]=1

Participants

4

Reactant 1

HCID 178514700HCID 178514700, compound

Product 1

HCID 178514701HCID 178514701, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (E)-2-{2-[2-(2-trifluoromethyl-phenyl)-vinyl]-1H-benzimidazol-5-yl}-benzenesulfonamide Cpd 364 (0.020 g, 0.045 mmol) and 10% palladium on charcoal (0.005 g, 0.0045 mmol) in 2 mL MeOH was hydrogenated under H2 gas (1 atm) for 1 hour. The catalyst was removed by filtration, the filtrate was concentrated to dryness, and the residue was purified by chromatography (silica gel, MeOH:CH2Cl2=10:1) to give the title compound as a white solid. 1H-NMR (400 MHz, CD3OD) δ (ppm): 8.14 (dd, 1H, J=1.2 and 7.6 Hz) 7.74-7.53 (m, 4H) 7.60-7.56 (m, 2H) 7.51-7.40 (m, 4H) 3.41 (m, 4H) MS (ESI, pos. ion) m/z: 446.5 (M+1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. customthe residue was purified by chromatography (silica gel, MeOH:CH2Cl2=10:1)

Sources & evidence

ORD record
ord-b34a3012832a4a4daffe92da91473693
Source dataset
uspto-grants-2011_05
Patent number
US07951829B2

Reaction notes

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