Isopropanol → HCID 19955596, compound

HRID 1779444Notes

Reaction equation

HRID 1779444 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([CH2:10][CH2:11][CH3:12])[NH:6][C:7]=1[CH:8]=[O:9])[CH3:2].[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[C:30](=[O:38])[C:31](=[O:37])[C:32]=2[O:33][CH:34]([CH3:36])[CH3:35])=[CH:19][CH:18]=1.CC(O)C>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:3]1[N:4]=[C:5]([CH2:10][CH2:11][CH3:12])[N:6]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[C:30](=[O:38])[C:31](=[O:37])[C:32]=3[O:33][CH:34]([CH3:36])[CH3:35])=[CH:21][CH:22]=2)[C:7]=1[CH:8]=[O:9])[CH3:2]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 19955579HCID 19955579, compoundHCID 178440054HCID 178440054, compound

Product 1

HCID 19955596HCID 19955596, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-ethyl-2-propyl-1H-imidazole-5-carboxaldehyde (0.15 g; preparable as described in WO92/00977; Dupont) in dry dimethylformamide (3 ml) was added sodium hydride (60% dispersion in mineral oil; 36 mg) and stirring was continued for approximately 45 minutes. The resulting solution was then added via canula to a stirred solution of 3-(4'-bromomethylbiphenyl-2-yl)-4-isopropoxycyclobut-3-ene-1,2-dione (0.35 g; preparable as in Example 1(c)) in dry dimethylformamide (3 ml). After stirring for 1 hour, 2-propanol (0.1 ml) was added. The mixture obtained was poured into ethyl acetate (20 ml) then washed with water (15 ml). The aqueous washings were extracted with ethyl acetate (10 ml) and the combined organic phases were washed with water (5×15 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure and the residue obtained was purified by flash chromatography on silica gel (eluting with ethyl acetate/petroleum ether (b.p. 60°-80° C.) (75:25)) to give 4-ethyl-1-[2'-(3,4-dioxo-2-isopropoxycyclobut-1-en-1-yl)biphenyl-4-ylmethyl]-2-propyl-1H-imidazole-5-carboxaldehyde, an active compound of the present invention, as a foam (0.194 g).

Workup

  1. stirringAfter stirring for 1 hour
  2. customThe mixture obtained
  3. washthen washed with water (15 ml)
  4. extractionThe aqueous washings were extracted with ethyl acetate (10 ml)
  5. washthe combined organic phases were washed with water (5×15 ml)
  6. dry with materialdried over magnesium sulphate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue obtained
  9. customwas purified by flash chromatography on silica gel (eluting with ethyl acetate/petroleum ether (b.p. 60°-80° C.) (75:25))

Sources & evidence

ORD record
ord-60d954afa4dd4e918a03ed3fef626fab
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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