Dimethylformamide → HCID 23024988, compound

HRID 350124Notes

Reaction equation

[CH:1]([C:4]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])=[CH:15][CH:14]=2)[N:5]=1)([CH3:3])[CH3:2].IC.[C:35](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:1]([C:4]1[C:8]([C:9]([O:11][CH3:35])=[O:10])=[CH:7][N:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])=[CH:17][CH:18]=2)[N:5]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-isopropyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-carboxylic acid (10.09 g), iodomethane (2 ml), potassium carbonate (4.83 g) and N,N-dimethylformamide (50 ml) was stirred at 80° C. for 5 hours. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-isopropyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-carboxylate (9.80 g, yield: 94%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 90–91° C.

Workup

extractionwas extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-18e6121447e54b29af11448833cdbf32
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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