Diisopropylethylamine → (5-{5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol

HRID 2247651Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15](=[N:17][OH:18])[NH2:16])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[C:19]1([C:25]2[CH:26]=[C:27]([C:34](Cl)=O)[S:28][C:29]=2[C:30]([F:33])([F:32])[F:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)C(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:19]1([C:25]2[CH:26]=[C:27]([C:34]3[O:18][N:17]=[C:15]([C:13]4[S:14][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=4)[N:16]=3)[S:28][C:29]=2[C:30]([F:33])([F:31])[F:32])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 2724141Tetrabutylammonium Fluoride

HCID 71711994-Phenyl-5-(trifluoromethyl)thiophene-2-carbonyl chloride

HCID 86620213HCID 86620213, compound

Product 1

HCID 68522049(5-{5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol

Procedure

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 1 (1e) using 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxythiophene-2-carboximidamide (0.43 g, 1.5 mmol) that was obtained in Example 4 (4b), 4-phenyl-5-(trifluoromethyl)thiophene-2-carbonyl chloride (0.52 g, 1.8 mmol), N,N-diisopropylethylamine (0.52 ml, 3.0 mmol), and a 1.0 M solution of tetrabutylammonium fluoride (3.0 ml, 3.0 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:2) as the eluent to afford the title compound (0.60 g) in a yield of 99% as a white crystalline solid.

Workup

customthe similar reaction to

Sources & evidence

ORD record: ord-625ac7192f8040ff9636667c09c7fdcd
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687491B2

Reaction notes

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