Triethylamine → 2-(6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

HRID 58940

반응식

HRID 58940 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=O.C(N(CC)CC)C.[C:31]1(=O)[CH2:36][CH2:35]CC[C:32]1=[O:37]>ClCCl.CN(C)C=O.CC(C)(O)C#N>[CH3:1][C:2]1[CH:3]=[C:4]([C:15]([CH:19]2[C:18](=[O:22])[CH2:35][CH2:36][CH2:31][C:32]2=[O:37])=[O:17])[C:5](=[O:14])[N:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

참가 물질

8

반응물 4

HCID 8471Triethylamine3회HCID 130061,2-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 127783026-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid

생성물 1

HCID 867092642-(6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6406Acetone Cyanohydrin촉매HCID 6344Dichloromethane용매2회

실험 절차

6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid (0.56 g, 2.42 mmol) was stirred in anhydrous dichloromethane (13 ml) and 1 drop of anhydrous dimethylformamide was added. Oxalyl chloride (0.25 mL, 2.90 mmol) was added dropwise to the yellow solution. After 1.5 h the reaction was concentrated in vacuo. The residue obtained was dissolved in dichloromethane (20 ml). To the brown solution anhydrous triethylamine (1 ml), then cyclohexanedione (0.33 g, 2.90 mmol) was added, producing a reddish solution. A further 0.33 ml of anhydrous triethylamine was added. The reaction mixture was stirred at room temperature for 2 h (reaction monitored by LCMS), then acetone cyanohydrin (1 drop) and anhydrous triethylamine (0.67 ml) was added and the reaction was stirred overnight. LCMS indicated the desired product had been formed. The reaction mixture was concentrated in vacuo. The residue obtained was purified using column chromatography (SiO2, Toluene/Triethylamine/Dioxane/EtOH/Water 100:40:20:20:5 by volume) to afford the title compound as an orange oil (382 mg, 49%). 1H NMR (CDCl3) 2.05 (quin, 2H), 2.41 (m, 3H), 2.47 (br s, 2H), 2.73 (br s, 2H), 7.10 (s, 1H), 7.36 (m, 1H), 7.46 (m, 2H), 7.57 (m, 2H), 16.15 (br s, 1H) ppm.

후처리

  1. concentrationAfter 1.5 h the reaction was concentrated in vacuo
  2. customThe residue obtained
  3. customproducing a reddish solution
  4. custom(reaction monitored by LCMS)
  5. stirringthe reaction was stirred overnight

출처 및 근거

ORD 기록
ord-96ccd2b2254043c3b501d501a6a37926
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09439428B2

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