Reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[F:13][C:14]([F:28])([F:27])[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][C:23]([NH:25][NH2:26])=[O:24])[CH:18]=[CH:19][CH:20]=1>O1CCCC1>[F:13][C:14]([F:27])([F:28])[C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][C:23]([NH:25][NH:26][C:10]([C:7]2[CH:8]=[CH:9][C:4]3[N:3]=[CH:2][S:1][C:5]=3[CH:6]=2)=[O:12])=[O:24])[CH:18]=[CH:19][CH:20]=1Participants
4
Procedure
To a solution of benzothiazole-6-carboxylic acid (358 mg, 2.00 mmol) in tetrahydrofuran (10 mL) was added N,N′-carbonyldiimidazole (341 mg, 2.10 mmol) at room temperature, and the resulting mixture was stirred for 1 hr. To this reaction mixture was added 3-[3-(trifluoromethyl)phenyl]propanohydrazide (557 mg, 2.40 mmol), and the mixture was further stirred at room temperature for 24 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The precipitate was collected by filtration, purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from hexane/tetrahydrofuran to give the title compound (524 mg, yield 67%) as colorless crystals.
Workup
- stirringthe mixture was further stirred at room temperature for 24 hr
- concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
- additionwas added to the residue
- filtrationThe precipitate was collected by filtration
- custompurified by basic silica gel column chromatography (tetrahydrofuran)
- customrecrystallized from hexane/tetrahydrofuran
Sources & evidence
- ORD record
- ord-a3a0ed6e055a466d858007180ec4798e
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492378B2
Linked notes
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