Tetrahydrofuran → (4-Ethyl-5-{5-[4-(3-fluorophenoxy)phenyl]-1,2,4-oxadiazol-3-yl}-2-thienyl)methanol
Reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15](=[N:17][OH:18])[NH2:16])=[C:12]([CH2:19][CH3:20])[CH:11]=1)(C(C)(C)C)(C)C.[F:21][C:22]1[CH:23]=[C:24]([CH:35]=[CH:36][CH:37]=1)[O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=O)=[CH:28][CH:27]=1.C1(N=C=NC2CCCCC2)CCCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:19]([C:12]1[CH:11]=[C:10]([CH2:9][OH:8])[S:14][C:13]=1[C:15]1[N:16]=[C:30]([C:29]2[CH:33]=[CH:34][C:26]([O:25][C:24]3[CH:35]=[CH:36][CH:37]=[C:22]([F:21])[CH:23]=3)=[CH:27][CH:28]=2)[O:18][N:17]=1)[CH3:20]Participants
Reactant 5
Product 1
Procedure
The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 10 (10f) using 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N′-hydroxythiophene-2-carboximidamide (0.16 g, 0.50 mmol) that was obtained in Example 10 (10d), 4-(3-fluorophenoxy)benzoic acid (0.13 g, 0.55 mmol) that was obtained in Example 17 (17a), N,N′-dicyclohexylcarbodiimide (0.11 g, 0.55 mmol), and 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.75 mL, 0.75 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 (3:7 to 5:5) as the eluent to afford the title compound (0.15 g) in a yield of 73% as a white crystalline solid.
Workup
- customthe reaction similar to
Sources & evidence
- ORD record
- ord-33e9a098027a4801a841d3b990890b57
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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