Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:22][C:21]([C:23]([OH:25])=O)=[CH:20][CH:19]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:38][CH:39]([NH2:43])[CH2:40][CH2:41][CH3:42]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:22][C:21]([C:23](=[O:25])[NH:43][CH:39]([CH3:38])[CH2:40][CH2:41][CH3:42])=[CH:20][CH:19]=1)=[O:17])([CH3:4])([CH3:3])[CH3:2]Participants
5
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 4.4 g (12.1 mmol) 5-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-thiophene-2-carboxylic acid in 80 ml THF were added 2.2 g (13.6 mmol) carbonyldiimidazol. The reaction mixture was stirred at 45° C. for 1 h and then cooled to rt. After addition of 1.05 g (12 mmol) 2-pentylamine the reaction mixture was kept at rt for 12 h. The solvent was evaporated and the residue was dissolved in 150 ml CH2Cl2. The solution was washed twice with 150 ml water each and dried over magnesium sulfate. The solvent was evaporated and the residue was washed with diethyl ether to yield (2-{[5-(1-methyl-butylcarbamoyl)-thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester as a white solid, mp. 183° C.
Workup
- temperaturecooled to rt
- waitwas kept at rt for 12 h
- customThe solvent was evaporated
- dissolutionthe residue was dissolved in 150 ml CH2Cl2
- washThe solution was washed twice with 150 ml water each and
- dry with materialdried over magnesium sulfate
- customThe solvent was evaporated
- washthe residue was washed with diethyl ether
Sources & evidence
- ORD record
- ord-b076af4194334424a356e8ccd3dc643f
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07501451B2
Linked notes
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