1-Benzylpiperazine → 6-(4-BENZYLPIPERAZIN-1-YL)PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDE

HRID 2356456Notes

Reaction equation

HRID 2356456 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11](Cl)=[CH:12][CH:13]=1)=[O:7].[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N12CCCN=C1CCCCC2>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[CH3:1][CH:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:26]2[CH2:27][CH2:28][N:23]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:24][CH2:25]2)=[CH:12][CH:13]=1)=[O:7]

Participants

6

Reactant 3

HCID 759941-BenzylpiperazineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 167337866-chloro-N-(3-methylbutyl)pyridazine-3-carboxamide

Product 1

HCID 865972166-(4-BENZYLPIPERAZIN-1-YL)PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDEYield 75.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture of 6-chloropyridazine-3-carboxylic acid (3-methylbutyl)amide (0.113 g, 0.5 mmol), 1-benzylpiperazine (90 mg, 0.5 mmol), tetrabutylammonium bromide (27 mg, 0.084 mmol) and 1,8-diazabicylco[5.4.0]undec-7-ene (152 mg, 1.0 mmol) was heated under reflux in dioxane (10 mL) overnight. The solvent was evaporated. Residue was treated with 2% methanol in water (25 mL). The solid, which precipitated, was filtered off and dried in vacuo to give 138 mg (0.376 mmol) of the title compound in 75% yield. 1H NMR (300 MHz, CDCl3) δ 7.98, 7.87, 7.36-7.32, 6.94, 3.76-3.74, 3.57, 3.50-3.46, 2.60-2.58, 1.74-1.68, 1.52-1.48, 0.94. MS (ES+) m/z 368.2 (M+1).

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. additionResidue was treated with 2% methanol in water (25 mL)
  4. customThe solid, which precipitated
  5. filtrationwas filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a5fd530113924a798bc2a62c4241c044
Source dataset
uspto-grants-2010_07
Patent number
US07759348B2

Reaction notes

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