HCID 22379953, compound → HCID 22380348, compound

HRID 895524Notes

Reaction equation

HRID 895524 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([NH2:12])=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:13][C:14]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[N:16]=[CH:17][CH:18]=1)[CH3:2]>C1(C)C=CC=CC=1.COC(O)C>[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]3[CH:1]=[N:3][CH:4]=[N:5]3)=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:13][C:14]1[N:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[N:16]=[CH:17][CH:18]=1)[CH3:2]

Participants

4

Reactant 1

HCID 22379953HCID 22379953, compound

Product 1

HCID 22380348HCID 22380348, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 30156371-MethoxyethanolSolvent

Procedure

1-Ethyl-2-{[2-(3-fluorophenyl)-pyrazol-3-yl]methyl}-5-amino-1H-benzimidazole (274 mg) is treated with N,N-dimethylformamide azine hydrochloride (1 eq) in toluene (10 mL) and methoxyethanol (10 mL) and refluxed for 6 h. After cooling and concentrating, the residue is treated with water and extracted with dichloromethane (2×). The aqueous layer is adjusted to pH 8 with aqueous sodium bicarbonate and extracted with dichloromethane (2×). The combined organic extracts are washed with saturated aqueous sodium chloride, dried (MgSO4), concentrated, purified by preparative silica gel chromatography, and triturated with ether to afford 1-Ethyl-2-{[2-(3-fluorophenyl)-pyrazol-3-yl]methyl}-5-(1,2,4-triazol-1-yl)-1H-benzimidazole, which is converted to the hydrochloride salt in ethyl acetate. LCMS MH+ 406.2.

Workup

  1. temperaturerefluxed for 6 h
  2. temperatureAfter cooling
  3. concentrationconcentrating
  4. additionthe residue is treated with water
  5. extractionextracted with dichloromethane (2×)
  6. extractionextracted with dichloromethane (2×)
  7. washThe combined organic extracts are washed with saturated aqueous sodium chloride
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. custompurified by preparative silica gel chromatography
  11. customtriturated with ether

Sources & evidence

ORD record
ord-7b896b8d285945269922e39d0d361b5b
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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