Tetrahydrofuran → {6-Ethyl-5-[5-(3-fluoro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methanol

HRID 2247779Notes

Reaction equation

HRID 2247779 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:37]([C:39]1[C:44]([C:45](=[N:47]O)[NH2:46])=[CH:43][CH:42]=[C:41]([CH2:49][O:50][Si](C(C)C)(C(C)C)C(C)C)[N:40]=1)[CH3:38].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:37]([C:39]1[N:40]=[C:41]([CH2:49][OH:50])[CH:42]=[CH:43][C:44]=1[C:45]1[N:47]=[C:5]([C:4]2[CH:8]=[CH:9][C:10]([CH2:11][CH:12]([CH3:14])[CH3:13])=[C:2]([F:1])[CH:3]=2)[O:7][N:46]=1)[CH3:38]

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 638867323-Fluoro-4-isobutylbenzoic acidHCID 866202272-Ethyl-N'-hydroxy-6-{[(triisopropylsilyl)oxy]methyl}pyridine-3-carboximidamide

Product 1

HCID 68522114{6-Ethyl-5-[5-(3-fluoro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}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-isobutylbenzoic acid (0.11 g, 0.54 mmol) that was obtained in Example 23 (23e), 1-hydroxybenzotriazole (86 mg, 0.56 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.11 g, 0.56 mmol), 2-ethyl-N′-hydroxy-6-{[(triisopropylsilyl)oxy]methyl}pyridine-3-carboximidamide (0.18 g, 0.51 mmol) that was obtained in Example 25 (25b), and a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.0 ml, 1.0 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 (2:8 to 4:6) as the eluent to afford the title compound (0.13 g) in a yield of 74% as a white crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-a3433073ce6c4ac0bbd4199fe9b0473c
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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