Tetrahydrofuran → {5-[5-(4-Isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]-6-methylpyridin-2-yl}methanol
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.O[N:38]=[C:39]([C:41]1[C:42]([CH3:59])=[N:43][C:44]([CH2:47][O:48][Si](C(C)C)(C(C)C)C(C)C)=[CH:45][CH:46]=1)[NH2:40].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][N:40]=[C:39]([C:41]3[CH:46]=[CH:45][C:44]([CH2:47][OH:48])=[N:43][C:42]=3[CH3:59])[N:38]=2)=[CH:7][C:6]=1[CH3:14])[CH:2]([CH3:3])[CH3:4]Participants
Reactant 6
HCID 8028Tetrahydrofuran
HCID 757711-Hydroxybenzotriazole
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 2724141Tetrabutylammonium Fluoride
HCID 592729384-Isobutyl-3-methylbenzoic acid
HCID 86620226N'-Hydroxy-2-methyl-6-{[(triisopropylsilyl)oxy]methyl}pyridine-3-carboximidamideProduct 1
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 (96 mg, 0.50 mmol) that was obtained in Example 27 (27d), 1-hydroxybenzotriazole (72 mg, 0.53 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.10 g, 0.53 mmol), N′-hydroxy-2-methyl-6-{[(triisopropylsilyl)oxy]methyl}pyridine-3-carboximidamide (0.16 g, 0.48 mmol) that was obtained in Example 24 (24d) 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 (1:2) as the eluent to afford the title compound (0.15 g) in a yield of 91% as a white crystalline solid.
Workup
- customthe similar reaction to
Sources & evidence
- ORD record
- ord-11c942ab4a394dc299db000fee4fb665
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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