Triethylamine → Phenyl N-(4-[2-(butyroylamino)pyridin-4-yl]oxyphenyl)carbamate

HRID 1433591Notes

Reaction equation

HRID 1433591 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

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 229364634-(4-Aminophenoxy)-2-butyrylaminopyridine

Product 1

HCID 58931168Phenyl N-(4-[2-(butyroylamino)pyridin-4-yl]oxyphenyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperaturecooled
  2. customThe cooling bath was removed
  3. additionSilica gel was added to the reaction solution
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionThe silica gel was charged into a dry column
  6. custompacked with silica gel, and column purification
  7. distillationThe solvent was distilled off under reduced pressure
  8. customto obtain the target substance as a colorless solid

Sources & evidence

ORD record
ord-46489ac996d3449486120656c60d6775
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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