Dichloromethane → [4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

HRID 1985637Notes

Reaction equation

HRID 1985637 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[N:9]1([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[OH-].[Na+].ClCCl>CN1C(=O)CCC1>[NH2:1][C:2]1[N:3]=[N:4][C:5]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:25])([F:24])[F:26])=[O:16])[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 216436-Amino-3-chloropyridazineHCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazine

Product 1

HCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanoneYield 52%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

The mixture of 3-amino-6-chloropyridazine (0.6487 g, 5 mmol) and piperazin-1-yl-(2-trifluoromethylphenyl)methanone (1.936 g, 7.5 mmol) in NMP (30 mL) was heated at 150° C. for 24 hours. To the reaction mixture was added 10 mL of 1 N NaOH and 100 mL of dichloromethane, and the aqueous layer was separated and extracted twice by 100 mL dichloromethane. The combined organic phase was dried over Na2SO4, evaporated to dryness. The crude compound was purified by flash chromatography to give yellow solid. Yield 52%, 1.37 g.

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted twice by 100 mL dichloromethane
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude compound was purified by flash chromatography
  6. customto give yellow solid

Sources & evidence

ORD record
ord-a0d14503d08e4996b52aa41c7240a2d0
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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