Ethylamine → HCID 59004204, compound

HRID 1696721Notes

Reaction equation

HRID 1696721 reaction equation
Br[C:2]1[CH: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.[NH:23]1CCC[C@H:24]1[C:25](O)=O.CCN.C([O-])([O-])=O.[K+].[K+]>O.[Cu]I.CS(C)=O>[CH2:24]([NH:23][C:2]1[CH:7]=[N:6][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])=[CH:4][CH:3]=1)[CH3:25]

Participants

8

Reactant 4

HCID 6341EthylamineHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 573569051-(5-Bromopyridin-2-yl)-5-methoxy-2-(trifluoromethyl)-1H-benzimidazole

Product 1

HCID 59004204HCID 59004204, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 10 ml sealed tube, was placed 1-(5-Bromo-pyridin-2-yl)-5-methoxy-2-trifluoromethyl-1H-benzoimidazole (30 g, 80.65 mmol). To this was added CuI (20 mg), L-Proline (20 g), CH3CH2NH2 (2 ml) and K2CO3 (30 g) followed by the addition of dimethylsulfoxide (DMSO) (6 ml). The resulting solution was allowed to stir for 6 hours at 60° C., then diluted with 10 ml of H2O and extracted two times with 30 ml of EtOAc. Organic layers were combined and washed with 20 ml of H2O. The combined organic layer was dried and concentrated, and the residue was purified by SGC using 1:12-1:6 EtOAc/petroleum ether as eluent to provide 21 g (78%) of Ethyl-[6-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyridin-3-yl]-amine (Compound 162) as a white solid.

Workup

  1. customInto a 10 ml sealed tube
  2. extractionextracted two times with 30 ml of EtOAc
  3. washwashed with 20 ml of H2O
  4. customThe combined organic layer was dried
  5. concentrationconcentrated
  6. customthe residue was purified by SGC

Sources & evidence

ORD record
ord-67dd5be0373649e5a735aa7b9a39c6bc
Source dataset
uspto-grants-2012_04
Patent number
US08163777B2

Reaction notes

Loading…