1-Bromo-2-butanone → HCID 11718339, compound

HRID 1985650Notes

Reaction equation

HRID 1985650 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Br[CH2:27][C:28](=O)[CH2:29][CH3:30].C(=O)(O)[O-].[Na+]>C(O)C>[CH2:29]([C:28]1[N:1]=[C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:9][CH2:10][N:11]([C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:12][CH2:13]3)=[N:6][N:7]2[CH:27]=1)[CH3:30]

Participants

5

Reactant 3

HCID 131561-Bromo-2-butanoneHCID 516892Sodium BicarbonateHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 11718339HCID 11718339, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)-methanone (0.120 g, 0.342 mmol), 1-bromobutan-2-one (0.077 g, 0.512 mmol) and sodium bicarbonate (0.016 g) in ethanol was refluxed over night. The reaction mixture was concentrated in vacuo, then diluted with 10 mL of water, extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by column chromatography. The title compound was obtained as a white solid in 69% yield (0.095 g). 1H NMR (300 MHz, CDCl3) δ 7.73-7.47 (m, 4H), 7.43 (s, 1H), 7.33 (d, J=7.5 Hz, 1H), 6.71 (d, J=7.5 Hz, 1H), 4.02-3.82 (m, 2H), 3.58-3.5 (m, 2H), 3.4-3.25 (m, 4H), 2.78 (q, 2H), 1.29 (m, J=7.5 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.5, 154.4, 148.1, 135.7, 134.44, 134.41, 132.3, 129.4, 127.2, 126.9, 126.8, 126.7, 125.4, 125.34, 121.8, 113.1, 109.4, 46:6, 46.4, 46.2, 41.2, 22.4, 13.5. MS (ES+)m/z 404 (M+1).

Workup

  1. temperaturewas refluxed over night
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with 10 mL of water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-779ab55d361c4600b96c8e77f2c9f767
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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