Acetic Acid → 1-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid (2-acetylamino-ethyl)-amide

HRID 919812ノート

反応式

HRID 919812 の反応式
CO[C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:7]([C:24]#[N:25])[N:6]=1)=[O:4].[NH2:26][CH2:27][CH2:28][NH:29][C:30](=[O:32])[CH3:31].CC(O)=O.O>CCO.CCOC(C)=O>[C:30]([NH:29][CH2:28][CH2:27][NH:26][C:3]([C:5]1[C:14]([OH:15])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:23])[N:12]2[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[C:7]([C:24]#[N:25])[N:6]=1)=[O:4])(=[O:32])[CH3:31]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 66082N-(2-aminoethyl)acetamideHCID 682972101-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester

生成物 1

HCID 867141221-Benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid (2-acetylamino-ethyl)-amide収率 35.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 1-benzyl-5-cyano-8-hydroxy-2-oxo-1,2-dihydro-[1,6]naphthyridine-7-carboxylic acid methyl ester (20 mg, 0.060 mmol) and N-(2-amino-ethyl)-acetamide (20 mg, 0.18 mmol) in EtOH (3 mL) was refluxed for 16 h. After cooling to r.t., AcOH (0.1 mL), water (15 mL) and EtOAc (20 mL) were added. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined, dried over MgSO4, and concentrated. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to give 8.7 mg of the title compound as a light yellow solid. MS: (−) m/z 404.32 (M−1).

後処理

  1. temperaturewas refluxed for 16 h
  2. extractionThe aqueous layer was extracted with additional EtOAc
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-a553adfa684043a6b500b801ebf53276
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

反応ノート

読み込み中…