Dimethylformamide → HCID 69429317, compound

HRID 1295329Notes

Reaction equation

[OH:1][C:2]1[C:6]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.Cl[CH2:21][C:22]1[CH:40]=[CH:39][C:25]([O:26][CH2:27][C:28]2[N:29]=[C:30]([C:34]3[O:35][CH:36]=[CH:37][CH:38]=3)[O:31][C:32]=2[CH3:33])=[C:24]([O:41][CH3:42])[CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:35]1[CH:36]=[CH:37][CH:38]=[C:34]1[C:30]1[O:31][C:32]([CH3:33])=[C:28]([CH2:27][O:26][C:25]2[CH:39]=[CH:40][C:22]([CH2:21][O:1][C:2]3[C:6]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:3]=3)=[CH:23][C:24]=2[O:41][CH3:42])[N:29]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 3-(3-hydroxy-1-phenyl-1H-pyrazol-4-yl)propionate (0.40 g), 4-(4-chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazole (0.57 g), potassium carbonate (276 mg) and N,N-dimethylformamide (10 ml) was stirred at 60° C. for 4 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazol-4-yl]propionate (420 mg, yield 44%) was obtained as colorless crystals-from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 97–98° C.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-6864f29cb2bf40979435c499d7c14e92
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241785B2

Reaction notes

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