Reaction equation
[Cl: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.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>>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][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: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 593167203-chloro-4-(2-methylpropyl)Benzoic 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 3-chloro-4-isobutylbenzoic acid (0.11 g, 0.50 mmol) that was obtained in Example 24 (24h), 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 tile compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1) as the eluent to afford the title compound (0.15 g) in a yield of 89% as a crystalline white solid.
Workup
- customthe similar reaction to
- customSubsequently, the crude product of the tile compound thus obtained
Sources & evidence
- ORD record
- ord-7e90ed963b164ced9d878663de276b20
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687491B2
Linked notes
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