Nalidixic Acid → 1-ethyl-7-methyl-4-oxo-N-(2-(pyridin-4-yl)ethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide

HRID 1290827ノート

反応式

HRID 1290827 の反応式
[CH3:1][CH2:2][N:3]1[C:9]2[N:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:15]([OH:17])=O)=[CH:4]1.ClCCl.C(OC(Cl)=O)(C)=C.[NH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C(N(CC)CC)C>[CH2:2]([N:3]1[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([CH3:14])[N:10]=2)[C:6](=[O:7])[C:5]([C:15]([NH:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[O:17])=[CH:4]1)[CH3:1]

参加物

6

反応物 4

HCID 4421Nalidixic AcidHCID 6344DichloromethaneHCID 832754-PyridineethanamineHCID 93846Isopropenyl chloroformate

生成物 1

HCID 99277371-ethyl-7-methyl-4-oxo-N-(2-(pyridin-4-yl)ethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

Nalidixic acid (0.45 g) and dichloromethane (20 ml) were combined and cooled to 0° C. under nitrogen. Triethylamine (0.3 ml) was then added, followed by isopropenylchloro-formate (0.24 ml) and the whole stirred for 90 minutes. 4-(2-Aminoethyl)pyridine (0.26 ml) was then added and stirring continued for 20 h, after which time the reaction was concentrated onto silica and purified by flash chromatography to give the title compound as an off white solid.

後処理

  1. stirringstirring
  2. waitcontinued for 20 h
  3. concentrationafter which time the reaction was concentrated onto silica
  4. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-95884ce208fd409b868d63e2a0eea073
出典データセット
uspto-grants-1998_05
特許番号
US05753666

反応ノート

読み込み中…