Butyrohydrazide → 1-Pyrimidin-2-yl-piperidine-4-carboxylic acid N'-butyryl-hydrazide

HRID 6911

Reaction equation

HRID 6911 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:39]([NH:44][NH2:45])(=[O:43])[CH2:40][CH2:41][CH3:42]>ClCCl.C(=O)([O-])O.[Na+]>[C:39]([NH:44][NH:45][C:13]([CH:10]1[CH2:9][CH2:8][N:7]([C:2]2[N:1]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:12][CH2:11]1)=[O:15])(=[O:43])[CH2:40][CH2:41][CH3:42]

Participants

7

Reactant 4

HCID 77079ButyrohydrazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27672671-(Pyrimidin-2-yl)piperidine-4-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 235440691-Pyrimidin-2-yl-piperidine-4-carboxylic acid N'-butyryl-hydrazideYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1-pyrimidin-2-yl-piperidine-4-carboxylic acid (3.0 g, 14.5 mmol)(see reference U.S. Pat. No. 4,826,843), 1-hydroxybenzotriazole hydrate (1.96 g, 14.5 mmol) and 1-(3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride (2.78 g, 14.5 mmol) in dichloromethane (100 ml) was stirred for 10 minutes. Butyric acid hydrazide (1.78 g, 17.4 mmol) was added and the reaction mixture was stirred under a nitrogen atmosphere for 18 hours. The reaction mixture was diluted with dichloromethane (100 ml) and sodium hydrogen carbonate solution was added. The reaction mixture was concentrated under reduced pressure and the solid formed was isolated by filtration. The material obtained was dried under vacuum at 40° C. to give the title compound (2.62 g).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe solid formed
  4. customwas isolated by filtration
  5. customThe material obtained
  6. customwas dried under vacuum at 40° C.

Sources & evidence

ORD record
ord-4e299013dbfd48c1bf2a6e7afd13ee69
Source dataset
uspto-grants-2006_08
Patent number
US07084145B2

Linked notes

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