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

HRID 1290827노트

반응식

HRID 1290827 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-95884ce208fd409b868d63e2a0eea073
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753666

반응 노트

불러오는 중…