Tetrahydrofuran → {5-[5-(3-Fluoro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methanol
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.[Si]([O:44][CH2:45][C:46]1[N:51]=[CH:50][C:49]([C:52](=[N:54]O)[NH2:53])=[CH:48][CH:47]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:54]=[C:52]([C:49]3[CH:48]=[CH:47][C:46]([CH2:45][OH:44])=[N:51][CH:50]=3)[N:53]=2)[CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]([CH3:14])[CH3:13]Participants
Reactant 6
HCID 8028Tetrahydrofuran
HCID 757711-Hydroxybenzotriazole
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 2724141Tetrabutylammonium Fluoride
HCID 638867323-Fluoro-4-isobutylbenzoic acid
HCID 866202256-({[t-Butyl(dimethyl)silyl]oxy}methyl)-N'-hydroxypyridine-3-carboximidamideProduct 1
Procedure
The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 12 (12a) using 3-fluoro-4-isobutylbenzoic acid (0.12 g, 0.63 mmol) that was obtained in Example 23 (23e), 1-hydroxybenzotriazole (89 mg, 0.66 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.13 g, 0.66 mmol), 6-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxypyridine-3-carboximidamide (0.17 g, 0.60 mmol) that was obtained in Example 23 (23c), and 1.0 M solution of tetrabutylammoniumfluoride in tetrahydrofuran (1.2 mL, 1.2 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 (2:3 to 1:1) as the eluent to afford the title compound (0.16 g) in a yield of 80% as a white crystalline solid.
Workup
- customthe reaction similar to
Sources & evidence
- ORD record
- ord-65687107f9ed475c952eba85989da90f
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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