Water → N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-(2-dimethylamino ethylaminomethyl)pyridine-2-carboxylic acid amide

HRID 217634노트

반응식

HRID 217634 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23]OS(C)(=O)=O)=[CH:19][N:18]=2)=[O:16])=[CH:11][S:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33].C(OCC)(=O)C.O>ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][NH:33][CH2:32][CH2:31][N:30]([CH3:34])[CH3:29])=[CH:19][N:18]=2)=[O:16])=[CH:11][S:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 66053N,N-DimethylethylenediamineHCID 86652250N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amide

생성물 1

HCID 67050142N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-(2-dimethylamino ethylaminomethyl)pyridine-2-carboxylic acid amide수율 28%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amide (Reference Compound No. 4-1, 0.36 g, 0.83 mmol) and N,N-dimethylethylenediamine (0.46 mL, 4.2 mmol) were dissolved in anhydrous dichloromethane (5.0 mL)-anhydrous acetonitrile (5.0 mL), and then the reaction mixture was stirred at room temperature for 1.5 hours. Ethyl acetate (0.10 L) and water (0.10 L) were added to the reaction solution, and then the mixture was partitioned. The organic layer was washed with brine (0.10 L), dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to give 98 mg of the title reference compound as a brown amorphous product. (Yield 28%)

후처리

  1. customthe mixture was partitioned
  2. washThe organic layer was washed with brine (0.10 L)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform-methanol)
  6. customto give 98 mg of the title reference compound as a brown amorphous product

출처 및 근거

ORD 기록
ord-ac18e52bda5d49e2849ba86806d2b12b
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198271B2

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