Isoniazid → 4-{2-Oxo-2-[N'-(pyridine-4-carbonyl)-hydrazino]-ethoxy}-piperidine-1-carboxylic acid tert-butyl ester

HRID 221346

반응식

HRID 221346 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]([OH:18])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[C:40]([NH:48][NH2:49])(=[O:47])[C:41]1[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][CH2:15][C:16](=[O:18])[NH:49][NH:48][C:40]([C:41]2[CH:46]=[CH:45][N:44]=[CH:43][CH:42]=2)=[O:47])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 3767IsoniazidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 15020822-((1-((Tert-butoxy)carbonyl)piperidin-4-yl)oxy)acetic acid

생성물 1

HCID 690777364-{2-Oxo-2-[N'-(pyridine-4-carbonyl)-hydrazino]-ethoxy}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4-carboxymethoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 1, 1.25 g, 4.82 mmol), ethyl-(3-dimethylaminopropyl)carbodiimide (924 mg, 4.82 mmol) and N-hydroxybenzotriazole (651 mg, 4.82 mmol) in anhydrous CH2Cl2 (30 ml) were stirred at rt for 10 min. Isonicotinic acid hydrazide (601 mg, 4.38 mmol) was added in one portion and stirring continued for a further 18 h. The reaction mixture was diluted with CH2Cl2 (150 ml) and washed with water (30 ml), saturated aqueous NaHCO3 (30 ml) and brine (30 ml). After drying (MgSO4) the solvent was removed to afford the title compound: RT=2.89 min; m/z (ES+)=379.1 [M+H]+.

후처리

  1. washwashed with water (30 ml), saturated aqueous NaHCO3 (30 ml) and brine (30 ml)
  2. dry with materialAfter drying (MgSO4) the solvent
  3. customwas removed

출처 및 근거

ORD 기록
ord-3a5f669f17e449a9b811e43de2843fcc
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207147B2

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