Water → HCID 54142092, compound

HRID 581976Notes

Reaction equation

HRID 581976 reaction equation
[CH3:1][N:2]([CH3:28])[CH:3]=[CH:4][C:5]([C:7]1[CH:27]=[CH:26][C:10]2[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][N:21]=4)[CH:15]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1)=[O:6].O>CN(C=O)C>[O:6]1[C:5]([C:7]2[CH:27]=[CH:26][C:10]3[N:11]([C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]5[CH:25]=[CH:24][N:23]=[CH:22][N:21]=5)[CH:15]=4)[CH:12]=[N:13][C:9]=3[CH:8]=2)=[CH:4][CH:3]=[N:2]1.[CH3:28][N:2]([CH3:1])[CH:3]=[CH:4][C:5]([C:7]1[CH:27]=[CH:26][C:10]2[N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][N:21]=4)[CH:15]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1)=[O:6]

Participants

5

Reactant 2

HCID 962WaterHCID 54142092HCID 54142092, compound

Product 2

HCID 53985945HCID 53985945, compoundHCID 54142092HCID 54142092, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(5-Isoxazolyl)-1-(3-(4-pyrimidinyl)phenyl)benzimidazole (45a) was prepared as follows: 5-(3-dimethylamino-1-oxo-2-propen-1-yl)-1-(3-(4-pyrimidinyl)phenyl)benzimidazole: (44b) (314 mg) was reacted with DMF-dimethylacetal (1.5 ml) under argon in DMF (3 ml) at 120° C. for 5 hours. After cooling to the mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with brine, dried, and concentrated under reduced pressure. The residue was purified by column-chromatography on silica gel using a mixture of CH2Cl2 and methanol (30:1) as the eluent to give 5-(3-dimethylamino-1-oxo-2-propen-1-yl)-1-(3-(4pyrimidinyl)phenyl)benzimidazole (320 mg, 87%).

Workup

  1. temperatureAfter cooling to the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column-chromatography on silica gel using
  7. additiona mixture of CH2Cl2 and methanol (30:1) as the eluent

Sources & evidence

ORD record
ord-bca6b17bfd6d47989c4a378b6cfb45c7
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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