Dimethylformamide → HCID 69420192, compound

HRID 350067Notes

Reaction equation

[OH:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:8]2)=[CH:4][CH:3]=1.Cl.Cl[CH2:29][C:30]1[N:31]=[C:32]([CH3:35])[S:33][CH:34]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:35][C:32]1[S:33][CH:34]=[C:30]([CH2:29][O:1][C:2]2[CH:26]=[CH:25][C:5]([CH2:6][N:7]3[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:9]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:8]3)=[CH:4][CH:3]=2)[N:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (349 mg), 4-chloromethyl-2-methylthiazole hydrochloride (276 mg), potassium carbonate (276 mg) and N,N-dimethylformamide (5 ml) was stirred at 90° C. for 6 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), and concentrated. The residue was subjected to silica gel column chromatograpy, and ethyl 3-[1-[4-(2-methyl-4-thiazolylmethoxy)benzyl]-4-phenyl-3-pyrrolyl]propionate (373 mg, yield: 81%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

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-f5d18471a85149219ca0559d07aa90da
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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