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

HRID 221346
Notes
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Reaction equation

HRID 221346 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-3a5f669f17e449a9b811e43de2843fcc
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08207147B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes