1-Hydroxybenzotriazole → (5-(5-(4-Isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl)pyridin-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.[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>[CH2:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][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:7][C:6]=1[CH3:14])[CH:2]([CH3:3])[CH3:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 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 (0.12 g, 0.61 mmol) that was obtained in Example 27 (27d), 1-hydroxybenzotriazole (86 mg, 0.64 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.12 g, 0.64 mmol), 6-({[t-butyl(dimethyl)silyl]oxy}methyl)-N′-hydroxypyridine-3-carboximidamide (0.16 g, 0.58 mmol) that was obtained in Example 23 (23c), and tetrabutylammonium fluoride (a 1.0 M solution 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 (0.19 g) in a yield of 99% as a white crystalline solid.
Workup
- customthe similar reaction to
Sources & evidence
- ORD record
- ord-8719682d7c624eb890000ae6645667a8
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Reaction notes
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