Water → HCID 68386921, compound

HRID 1051174Notes

Reaction equation

HRID 1051174 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:18][CH2:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C:5]2[N:9]=[CH:8][N:7](C(OC(C)(C)C)=O)[C:6]=2[CH:17]=1.O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:18][CH2:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68386696HCID 68386696, compound

Product 1

HCID 68386921HCID 68386921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of intermediate tert-butyl 6-bromo-4-[(3,3,3-trifluoropropyl)amino]-1H-benzimidazole-1-carboxylate (7.63 g, 18.69 mmol) in DCM (200 mL) at -rt was added water (20 mL) and TFA (200 mL). After stirring for 2 h, the solution was concentrated, ethyl acetate was added and the organic phase was washed with sodium carbonate solution and water. Evaporation of the yielded 5.17 g 6-bromo-N-(3,3,3-trifluoropropyl)-1H-benzimidazol-4-amine (89.8%).

Workup

  1. concentrationthe solution was concentrated
  2. additionethyl acetate was added
  3. washthe organic phase was washed with sodium carbonate solution and water
  4. customEvaporation of the yielded 5.17 g 6-bromo-N-(3,3,3-trifluoropropyl)-1H-benzimidazol-4-amine (89.8%)

Sources & evidence

ORD record
ord-ba3358b49e8d416fbb45dd360f36c12e
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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