HCID 67387379, compound → HCID 67387004, compound

HRID 2098244Notes

Reaction equation

HRID 2098244 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=2)[CH:7]=[CH:8][C:9]=1[NH2:10])([O-])=O>CO.[Pd]>[F:19][C:18]([F:20])([F:21])[O:17][C:13]1[CH:12]=[C:11]([C:6]2[CH:7]=[CH:8][C:9]([NH2:10])=[C:4]([NH2:1])[CH:5]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 67387379HCID 67387379, compound

Product 1

HCID 67387004HCID 67387004, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Nitro-3′-trifluoromethoxy-biphenyl-4-ylamine (28.5 g) was dissolved in methanol (250 mL). To this solution, Pd—C (10%, Degussa Type, 15 g) was added, and the resulting mixture was stirred under a hydrogen atmosphere for 4 hours. The solution was filtered on celite, washed with methanol, and then concentrated to give 3′-trifluoromethoxy-biphenyl-3,4-diamine (17.8 g) which was used without further purification. 3′-Trifluoromethoxy-biphenyl-3,4-diamine (17.8 g) was taken up into methanol (100 mL), and cyanogen bromide (8.9 g) was added. The resulting mixture was stirred at room temperature for about 30 minutes. The solution was concentrated to dryness. The resulting crude product was triturated with diethyl ether (100 mL), filtered and dried to obtain 5-(3-trifluoromethoxy-phenyl)-1H-benzoimidazol-2-ylamine hydrobromide salt (21.3 g), which was used without further purification. LCMS (m/z): 293.9.

Workup

  1. filtrationThe solution was filtered on celite
  2. washwashed with methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b7046d0de7a24b09a59e472bfe7b4787
Source dataset
uspto-grants-2013_05
Patent number
US08450354B2

Reaction notes

Loading…