Triethylamine → HCID 86024941, compound

HRID 499144Notes

Reaction equation

HRID 499144 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[N:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:13][CH:14]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>ClCCl>[Cl:8][C:9]1[N:10]=[N:11][C:12]([N:15]2[CH2:16][CH2:17][N:18]([C:25]([C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[C:22]([F:21])([F:32])[F:33])=[O:26])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 52949263-Chloro-6-(1-piperazinyl)pyridazine

Product 1

HCID 86024941HCID 86024941, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.0 mL) was added to an ice cold solution of 3-chloro-6-piperazin-1-ylpyridazine (1.00 g, 6.69 mmol) in dichloromethane (10 mL), followed by the addition of 2-trifluoromethylbenzoyl chloride (2.10 g, 10.03 mmol). The mixture was allowed to warm up to room temperature and then stirred for 30 minutes. The solvent was removed in vacuo and the crude mixture was dissolved in ethyl acetate (15 mL), washed with water and dried over anhydrous Na2SO4. [4-(6-chloropyridazin-3-yl)piperazin-1-yl]-(2-trifluoromethylphenyl)methanone was obtained as a thick liquid after purified by column chromatography in 79% yield (1.96 g). 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=7.9 Hz, 1H), 7.63-7.50 (m, 2H), 7.32 (d, J=7.3 Hz, 1H), 7.21 (t, J=4.4 Hz, 1H), 6.92 (d, J=9.5 Hz, 1H), 4.20-3.92 (m, 1H), 3.92-3.80 (m, 1H), 3.70-3.55 (m, 4H), 3.30 (t, J=5.3 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 167.6, 158.7, 147.7, 134.2, 134.2, 132.3, 129.5, 129.1, 127.2, 126.8, 126.8, 115.6, 46.3, 45.2, 44.7, 41.2. MS (ES+) m/z 371.1 and 373.1 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe crude mixture was dissolved in ethyl acetate (15 mL)
  3. washwashed with water
  4. dry with materialdried over anhydrous Na2SO4

Sources & evidence

ORD record
ord-55dea1ee0255481fa759d656bc5f1767
Source dataset
uspto-grants-2010_08
Patent number
US07767677B2

Reaction notes

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