Imidazole → HCID 178447256, compound

HRID 2247911Notes

Reaction equation

HRID 2247911 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=[C:6]2[OH:20].[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>C(#N)C>[OH:20][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH2:2][N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)[CH:4]=2)[N:9]=[C:8]([NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 178447250HCID 178447250, compound

Product 1

HCID 178447256HCID 178447256, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 13 parts of N-[6-(bromomethyl)-4-hydroxy-2-quinazolinyl]-2,2-dimethylpropanamide, 15.5 parts of 1H-imidazole and 80 parts of acetonitrile was stirred for 4 hours at reflux temperature. The reaction mixture was evaporated and the residue was extracted with ethyl acetate. The extract was washed with NaHCO3 (aq.), dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2). The eluent of the desired fraction was evaporated, yielding 4.3 parts (34.7%) of N-[4-hydroxy-6-(1H-imidazol-1-ylmethyl)-2-quinazolinyl]-2,2-dimethylpropanamide (interm. 69).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with NaHCO3 (aq.)
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2)
  9. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-06c81d342bcb44cc8a6757fab2eadf6e
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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