Triethylamine → Phenyl N-(4-[2-(butyroylamino)pyridin-4-yl]oxyphenyl)carbamate
Reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1[CH:30]=[CH:29][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:28])[CH2:25][CH2:26][CH3:27])[CH:18]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>O1CCCC1>[C:24]([NH:23][C:19]1[CH:18]=[C:17]([O:16][C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:2](=[O:3])[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:30][CH:29]=2)[CH:22]=[CH:21][N:20]=1)(=[O:28])[CH2:25][CH2:26][CH3:27]Participants
5
Procedure
Phenyl chloroformate (0.14 ml) was added dropwise to an ice-cooled stirred solution of 4-(4-aminophenoxy)-2-(butyrylamino)pyridine (0.3 g), triethylamine (0.14 ml) and tetrahydrofuran (10 ml). The cooling bath was removed and the mixture was stirred at room temperature overnight. Silica gel was added to the reaction solution, the solvent was distilled off under reduced pressure and the reaction product was adsorbed onto the silica gel. The silica gel was charged into a dry column packed with silica gel, and column purification was performed (hexane:ethyl acetate=2:1, followed by 1:1). The solvent was distilled off under reduced pressure to obtain the target substance as a colorless solid.
Workup
- temperaturecooled
- customThe cooling bath was removed
- additionSilica gel was added to the reaction solution
- distillationthe solvent was distilled off under reduced pressure
- additionThe silica gel was charged into a dry column
- custompacked with silica gel, and column purification
- distillationThe solvent was distilled off under reduced pressure
- customto obtain the target substance as a colorless solid
Sources & evidence
- ORD record
- ord-655358974d3d4841a1cf785bbe1329aa
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973160B2
Reaction notes
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