HCID 11245451, compound → HCID 11450452, compound

HRID 1991207Notes

Reaction equation

HRID 1991207 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[O:15])[CH:11]=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CO>[NH2:1][C:4]1[C:9]2[N:10]([CH2:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:26])[F:24])[CH:18]=3)=[O:15])[CH:11]=[N:12][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 11245451HCID 11245451, compound

Product 1

HCID 11450452HCID 11450452, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(7-nitro-1H-benzoimidazol-1-yl)-N-[3-(trifluoromethyl)phenyl]acetamide, described above, (0.4 g, 1.1 mmol) in methanol (15 mL) 10% Pd/C (60 mg) was added. The mixture was hydrogenated at atmospheric pressure until the consumption of hydrogen ceased (1 h). The catalyst was removed by filtration through Celite, and the resulting clear solution was concentrated to dryness to yield the title compound, 0.36 g (99%). MS (ESI) m/z: 335.07 [M+H]. 1H NMR (400 MHz, DMSO-D6) δ ppm 4.91 (s, 2H) 5.33 (s, 2H) 6.50 (m, 1H) 6.89 (t, J=7.6 Hz, 1H) 6.97 (m, 1H) 7.41 (d, J=7.6 Hz, 1H) 7.56 (t, J=7.8 Hz, 1H) 7.77 (m, 1H) 7.99 (s, 1H) 8.07 (s, 1H) 10.84 (s, 1H).

Workup

  1. customThe mixture was hydrogenated at atmospheric pressure until the consumption of hydrogen
  2. custom(1 h)
  3. customThe catalyst was removed by filtration through Celite
  4. concentrationthe resulting clear solution was concentrated to dryness

Sources & evidence

ORD record
ord-18438d53b82d4b9ea1bee17fa7940170
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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