Tetrahydrofuran → (6-Ethyl-5-(5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methanol

HRID 2247776Notes

Reaction equation

HRID 2247776 reaction equation
[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[CH3:14])[CH:2]([CH3:4])[CH3:3].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:9]([C:8]2[CH:12]=[CH:13][C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])=[C:6]([CH3:14])[CH:7]=2)[O:11][N:46]=1)[CH3:38]

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724141Tetrabutylammonium FluorideHCID 592729384-Isobutyl-3-methylbenzoic acidHCID 866202272-Ethyl-N'-hydroxy-6-{[(triisopropylsilyl)oxy]methyl}pyridine-3-carboximidamide

Product 1

HCID 68522833(6-Ethyl-5-(5-(4-isobutyl-3-methylphenyl)-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 4-isobutyl-3-methylbenzoic acid (92 mg, 0.48 mmol) that was obtained in Example 27 (27d), 1-hydroxybenzotriazole (69 mg, 0.51 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (97 mg, 0.51 mmol), 2-ethyl-N′-hydroxy-6-{[(triisopropylsilyl)oxy]methyl}pyridine-3-carboximidamide (0.16 g, 0.46 mmol) that was obtained in Example 25 (25b), and a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.92 ml, 0.92 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 (0.15 g) in a yield of 93% as a white crystalline solid.

Workup

  1. customthe similar reaction to

Sources & evidence

ORD record
ord-4b20a783026144d39f202984c026e48f
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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