Tetrahydrofuran → {4-Ethyl-5-[5-(3-fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol

HRID 2247705Notes

Reaction equation

HRID 2247705 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([OH:7])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Si]([O:47][CH2:48][C:49]1[S:53][C:52]([C:54](=[N:56]O)[NH2:55])=[C:51]([CH2:58][CH3:59])[CH:50]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:58]([C:51]1[CH:50]=[C:49]([CH2:48][OH:47])[S:53][C:52]=1[C:54]1[N:56]=[C:5]([C:4]2[CH:8]=[CH:9][C:10]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:2]([F:1])[CH:3]=2)[O:7][N:55]=1)[CH3:59]

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 286051153-Fluoro-4-phenoxybenzoic acidHCID 725011755-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N'-hydroxythiophene-2-carboximidamide

Product 1

HCID 68525233{4-Ethyl-5-[5-(3-fluoro-4-phenoxyphenyl)-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 12 (12a) using 3-fluoro-4-phenoxybenzoic acid (0.12 g, 0.50 mmol) that was obtained in Example 11 (11e), 1-hydroxybenzotriazole (72 mg, 0.53 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.10 g, 0.53 mmol), 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N′-hydroxythiophene-2-carboximidamide (0.15 g, 0.48 mmol) that was obtained in Example 10 (10d), and a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.96 ml, 0.96 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 (1:3) as the eluent to afford the title compound (0.16 g) in a yield of 85% as a pale yellowish crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-75449c8b17c2423b82b0588fb6aa3954
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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