Triethylamine → [4-(6-Pyridin-2-ylpyridazin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone

HRID 499170Notes

Reaction equation

HRID 499170 reaction equation
[N:1]1([C:7]2[N:8]=[N:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:11][CH:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>ClCCl>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[N:9]=[N:8][C:7]([N:1]2[CH2:2][CH2:3][N:4]([C:30]([C:29]3[CH:33]=[CH:34][CH:35]=[CH:36][C:28]=3[C:27]([F:26])([F:37])[F:38])=[O:31])[CH2:5][CH2:6]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 336763413-Piperazin-1-yl-6-pyridin-2-ylpyridazine

Product 1

HCID 11596773[4-(6-Pyridin-2-ylpyridazin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanoneYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-piperazin-1-yl-6-pyridin-2-ylpyridazine (0.240 g, 1.000 mmol) and triethylamine (0.7 mL) in dichloromethane (15 mL) at room temperature was added 2-trifluoromethylbenzoyl chloride (0.210 g, 1.000 mmol). After 15 minutes, the mixture was washed with citric acid and NaHCO3. The organic layer was separated, dried over anhydrous MgSO4 and evaporated to yield solid residue, which was crystallized from ether to afford the title compound as a white solid in 23% yield (0.097 g). 1H NMR (300 MHz, CDCl3) δ 8.6 (d, J=4.4 Hz, 1H), 8.5 (d, J=8.0 Hz, 1H), 8.3 (d, J=9.5 Hz, 1H), 7.8 (m, 1H), 7.7 (d, J=7.7 Hz, 1H), 7.6 (t, J=7.3 Hz, 1H), 7.5 (t, J=7.5 Hz, 1H), 7.35 (d, J=7.3 Hz, 1H), 7.28 (m, 1H), 7.0 (d, J=9.5 Hz, 1H), 4.1-3.6 (m, 6H), 3.35-3.31 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 159.3, 153.9, 151.4, 148.9, 137.0, 134.4, 132.3, 127.3, 126.8, 123.6, 120.3, 113.1, 46.5, 44.9, 44.6, 41.3. MS (ES+) m/z 414.1 (M+1).

Workup

  1. washthe mixture was washed with citric acid and NaHCO3
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated
  5. customto yield solid residue, which
  6. customwas crystallized from ether

Sources & evidence

ORD record
ord-cf577922c79c48ea870666ab2ea28502
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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