Methanol → 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid propylamide

HRID 1514855Notes

Reaction equation

HRID 1514855 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19](Cl)=[O:20])[CH:16]=[CH:15][C:13]=2[N:14]=1.[CH2:22]([NH2:25])[CH2:23][CH3:24].CCN(C(C)C)C(C)C.CO>C(#N)C>[CH2:22]([NH:25][C:19]([C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([C:4]3[C:5]([Cl:9])=[CH:6][CH:7]=[CH:8][C:3]=3[Cl:2])[NH:11][C:12]=2[CH:18]=1)=[O:20])[CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 866328172-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride

Product 1

HCID 250663812-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid propylamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carbonyl chloride hydrochloride salt in acetonitrile (0.2 M, 0.10 mL) was added to a vial containing n-propylamine (0.2 M in toluene, 0.11 mL) and DIPEA (0.5M in toluene, 0.10 mL). After incubation on a shaker at ambient temperature overnight, the mixture was diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid propylamide: MS (m/z) 347.95 (M+1).

Workup

  1. additionwas added to
  2. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  3. washWash-to-waste (5 mL MeOH)
  4. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  5. customafter evaporation of volatiles
  6. customthe crude was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-73b335ff5b1540748bd25ebbc26aa721
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…