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

HRID 2063324ノート

反応式

HRID 2063324 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-fe7bfeb528f844e9bfc81ead1b09f485
出典データセット
uspto-grants-2012_10
特許番号
US08288380B2

反応ノート

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