2,6-Difluorobenzoic acid → HCID 24850494, compound

HRID 1696725Notes

Reaction equation

HRID 1696725 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]2[N:7]([C:14]3[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=3)[C:8]([C:10]([F:13])([F:12])[F:11])=[N:9][C:5]=2[CH:4]=1.[F:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:25]=1[C:26](O)=[O:27].CN(C)CCCN=C=NCC>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[F:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:25]=1[C:26]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([N:7]2[C:6]3[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:9]=[C:8]2[C:10]([F:13])([F:11])[F:12])=[CH:19][N:18]=1)=[O:27]

Participants

6

Reactant 3

HCID 97962,6-Difluorobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 573569065-[5-Methoxy-2-(trifluoromethyl)-1H-benzimidazol-1-yl]pyridin-2-amine

Product 1

HCID 24850494HCID 24850494, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of 5-(5-methoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyridin-2-amine (80 mg, 0.25 mmol) in CHCl3 (10 ml) was added 2,6-difluorobenzoic acid (90 mg, 0.57 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (240 mg, 1.25 mmol) and 4-dimethylaminopyridine (DMAP) (160 mg, 1.31 mmol). The resultant solution was allowed to stir for 24 hours at room temperature. The reaction progress was monitored by TLC (EtOAc/petroleum ether=1:1). After the completion, the resultant solution was diluted with 30 ml of CHCl3 and washed with 30 ml of H2O. The mixture was dried and concentrated by evaporation under reduced pressure on a rotary evaporator. The crude product was purified by SGC using 1:5 EtOAc/petroleum ether as eluent to afford 90 mg (81%) of 2,6-difluoro-N-(5-(5-methoxy-2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)pyridin-2-yl)benzamide (Compound 163) as a white solid.

Workup

  1. washwashed with 30 ml of H2O
  2. customThe mixture was dried
  3. concentrationconcentrated by evaporation under reduced pressure on a rotary evaporator
  4. customThe crude product was purified by SGC

Sources & evidence

ORD record
ord-773de39ec4434aca881b3cdbcaa717e4
Source dataset
uspto-grants-2012_04
Patent number
US08163777B2

Reaction notes

Loading…