Hydrochloric Acid → HCID 21876238, compound

HRID 858522Notes

Reaction equation

HRID 858522 reaction equation
[Cl:1][C:2]1[C:3]([NH:22][CH:23]=O)=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][Cl:20])=[CH:14][CH:13]=3)[C:6]=2[CH:21]=1.S(C)C.CO.Cl>C1COCC1>[Cl:1][C:2]1[C:3]([NH:22][CH3:23])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][Cl:20])=[CH:16][CH:17]=3)[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1068Dimethyl SulfideHCID 86611506HCID 86611506, compound

Product 1

HCID 21876238HCID 21876238, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6-chloro-1-[4-(2-chloroethyl)phenyl]-2-ethyl-1H-benzimidazol-5-ylformamide, step 1, 112 mg, 0.3 mmol) in THF (15 ml) was added Me2S BH3 (0.07 ml, 0.77 mmol) under nitrogen at room temperature. The mixture was refluxed for 1 h. Then the mixture was cooled to room temperature and was added methanol (3 ml) and 2N aqueous HCl (12 ml). The mixture was stirred at 70° C. for 30 min. The volatile component was removed under reduced pressure, and the residue was dissolved with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous NaHCO3 (50 ml), brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (1:4) to afford 93 mg (87%) of the title compound as white solids.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. customThe volatile component was removed under reduced pressure
  3. dissolutionthe residue was dissolved with ethyl acetate (100 ml)
  4. washThe organic layer was washed with saturated aqueous NaHCO3 (50 ml), brine (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customAfter removal of solvent
  7. customthe crude product was purified by flash column chromatography
  8. washeluting with hexane/ethyl acetate (1:4)

Sources & evidence

ORD record
ord-6667113a83ba440e9d67a62dacdccfdb
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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