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

HRID 2247709Notes

Reaction equation

HRID 2247709 reaction equation
[Cl: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>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:56]=[C:54]([C:52]3[S:53][C:49]([CH2:48][OH:47])=[CH:50][C:51]=3[CH2:58][CH3:59])[N:55]=2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 570419363-Chloro-4-phenoxybenzoic acidHCID 725011755-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N'-hydroxythiophene-2-carboximidamide

Product 1

HCID 68525760{5-[5-(3-Chloro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-4-ethyl-2-thienyl}methanol

Procedure

The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 12 (12a) using 3-chloro-4-phenoxybenzoic acid (0.12 g, 0.50 mmol) that was obtained in Example 15 (15a), 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 1.0 M solution of tetrabutylammoniumfluoride 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 (0.17 g) in a yield of 87% as a pale yellow crystalline solid.

Workup

  1. customthe reaction similar to

Sources & evidence

ORD record
ord-f5cbd1eece5b4024bbbb31c552f149be
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

Loading…