Tetrahydrofuran → Tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methylidene}amino)benzoyl]carbamoyl}hydrazinecarboxylate
Reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]([NH:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:9])=[CH:4][CH:3]=1.[CH:21]([C:23]1[N:24]=[C:25]([NH:28][C:29](=[O:31])[CH3:30])[S:26][CH:27]=1)=O.[O:32]1CCCC1>>[C:29]([NH:28][C:25]1[S:26][CH:27]=[C:23]([CH:21]=[N:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([NH:7][C:8]([NH:10][NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])=[O:9])=[O:32])=[CH:19][CH:20]=2)[N:24]=1)(=[O:31])[CH3:30]Participants
4
Procedure
To a solution of tert-butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate (700.7 mg, 2.500 mmol) in anhydrous tetrahydrofuran (10 ml) was added N-(4-formyl-1,3-thiazol-2-yl)acetamide (425.5 mg, 2.500 mmol). The mixture was heated under reflux for 1 hr, cooled to room temperature, and concentrated under reduced pressure. Tetrahydrofuran (5 ml) and tert-butyl methyl ether (10 ml) were added to the residue and the mixture was stirred. The resulting solid was collected by filtration, washed twice with tert-butyl methyl ether and dried under reduced pressure to give tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]methylidene}amino)benzoyl]carbamoyl}hydrazinecarboxylate (1.097 g, quantitative) as a white solid.
Workup
- temperatureThe mixture was heated
- temperatureunder reflux for 1 hr
- concentrationconcentrated under reduced pressure
- additionTetrahydrofuran (5 ml) and tert-butyl methyl ether (10 ml) were added to the residue
- filtrationThe resulting solid was collected by filtration
- washwashed twice with tert-butyl methyl ether
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-7fcc5148c9814d6fb4894ed425f7bae6
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507690B2
Reaction notes
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