Sodium hydride → HCID 19955590, compound

HRID 1779447Notes

Reaction equation

HRID 1779447 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[C:32](=[O:40])[C:33](=[O:39])[C:34]=2[O:35][CH:36]([CH3:38])[CH3:37])=[CH:21][CH:20]=1>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[C:32](=[O:40])[C:33](=[O:39])[C:34]=3[O:35][CH:36]([CH3:38])[CH3:37])=[CH:23][CH:24]=2)[C:7]([C:11]([O:13][CH3:14])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19955579HCID 19955579, compoundHCID 178441706HCID 178441706, compound

Product 1

HCID 19955590HCID 19955590, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl 2-butyl-4-chloro-1H-imidazole-5-carboxylate (0.19 g) was added to a stirring suspension of sodium hydride (60% dispersion in mineral oil; 35 mg) in dry dimethylformamide (2 ml) at ambient temperature under a nitrogen atmosphere and stirring was continued for 30 minutes. A solution of 3-(4'-bromomethylbiphenyl-2-yl)-4-isopropoxycyclobut-3-ene-1,2-dione (0.64 g; preparable as in Example 1(c)) in dry dimethyl formamide (3 ml) was added and stirring was continued for 24 hours. The reaction mixture was partitioned between water (20 ml) and diethyl ether (20 ml), and the aqueous layer was separated and extracted with diethyl ether (20 ml). The combined ether solutions were dried over magnesium sulphate and the solvent was evaporated in vacuo. The residue obtained was purified by flash chromatography on silica gel (eluting with 20% ethyl acetate in petroleum ether (b.p. 40°-60° C.)) to give methyl 2-butyl-4-chloro-1-[2'-(2-isopropoxy-3,4-dioxocyclobut-1-en-1-yl)biphenyl-4-ylmethyl]-1H-imidazole-5-carboxylate, an active compound of the present invention, as a yellow oil (0.17 g).

Workup

  1. stirringstirring
  2. waitwas continued for 24 hours
  3. customThe reaction mixture was partitioned between water (20 ml) and diethyl ether (20 ml)
  4. customthe aqueous layer was separated
  5. extractionextracted with diethyl ether (20 ml)
  6. dry with materialThe combined ether solutions were dried over magnesium sulphate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by flash chromatography on silica gel (eluting with 20% ethyl acetate in petroleum ether (b.p. 40°-60° C.))

Sources & evidence

ORD record
ord-524c28253cd8441bba669710d18b8330
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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