Ammonia → 5-(5-Methoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyrazin-2-amine

HRID 1642273Notes

Reaction equation

HRID 1642273 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]([F:22])([F:21])[F:20])=[N:6][CH:7]=1.[NH3:23]>C(O)CO.O>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([C:5]3[N:6]=[CH:7][C:2]([NH2:23])=[N:3][CH:4]=3)[C:9]([C:19]([F:22])([F:21])[F:20])=[N:10][C:11]=2[CH:16]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 573569041-(5-Bromopyrazin-2-YL)-2-(trifluoromethyl)-5-methoxy-1H-benzo[D]imidazole

Product 1

HCID 534878715-(5-Methoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyrazin-2-amineYield 40%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Into a 10 mL sealed tube, was placed 1-(5-bromo-pyrazin-2-yl)-5-methoxy-2-trifluoromethyl-1H-benzoimidazole (iv) (150 mg, 0.40 mmol). To this was added Cu2O (30 mg, 0.21 mmol), followed by a saturated solution of NH3 in ethylene glycol (4 ml). The resulting solution was stirred at 70° C. for 3 hours, then diluted with 30 mL of H2O and extracted three times with 20 mL of EtOAc. The organic layers were combined and dried over Na2SO4. Removal of the volatile components under reduced pressure afforded the product 5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyrazin-2-ylamine (v) (50 mg, yield 40%) as a white solid.

Workup

  1. customInto a 10 mL sealed tube
  2. extractionextracted three times with 20 mL of EtOAc
  3. dry with materialdried over Na2SO4
  4. customRemoval of the volatile components under reduced pressure

Sources & evidence

ORD record
ord-74deb1993ed04f11b1900baa3ed32cbf
Source dataset
uspto-grants-2012_02
Patent number
US08119643B2

Reaction notes

Loading…