2,4-Pentanedione, 3-benzyl- → 4-(4-Benzyl-3,5-dimethyl-pyrazol-1-yl)-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine

HRID 1410391

반응식

HRID 1410391 반응식
[NH:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH2:15])[N:4]=1)[NH2:2].[CH2:16]([CH:23]([C:27](=O)[CH3:28])[C:24](=O)[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.C(Cl)Cl.C(OCC)(=O)C>[CH2:16]([C:23]1[C:24]([CH3:25])=[N:2][N:1]([C:3]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[N:6]=[C:5]([NH2:15])[N:4]=2)[C:27]=1[CH3:28])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

참가 물질

7

반응물 3

HCID 977572,4-Pentanedione, 3-benzyl-HCID 521998p-Toluenesulfonic acid monohydrateHCID 6089524-Hydrazinyl-6-(pyridin-2-yl)-1,3,5-triazin-2-amine

생성물 1

HCID 221748704-(4-Benzyl-3,5-dimethyl-pyrazol-1-yl)-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

A suspension of 4-hydrazino-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine (5.25 g, 25.6 mmol), 3-benzylpentane-2,4-dione (5.0 g, 28.4 mmol), and p-toluenesulfonic acid monohydrate (0.475 g, 2.50 mmol) in dimethylsulfoxide (50 mL) was heated to 75° C. for 20 hours. The reaction mixture was allowed to cool to room temperature, and the suspension was dissolved in methylene chloride (700 mL). The solution was washed three times with water, once with brine, dried (magnesium sulfate), and concentrated to afford a moist solid. The crude product was suspended in ethyl acetate (50 mL), heated to reflux, allowed to cool to room temperature, and filtered (repeated three times). The final product was obtained as a white solid containing 3% dimethylsulfoxide by weight: 8.63 g (90%). 1H NMR (CDCl3) δ 8.84-8.53 (m, 1H), 8.48 (d, J=7.9 Hz, 1H), 7.86-7.91 (m, 1H), 7.46-7.50 (m, 1H), 7.13-7.30 (m, 5H), 6.61 (br s, 1H), 6.40 (br s, 1H), 3.83 (s, 2H), 2.79 (s, 3H), 2.24 (s, 3H) ppm. MS (ESI) m/z 358 (M+H+).

후처리

  1. temperatureto cool to room temperature
  2. washThe solution was washed three times with water
  3. dry with materialonce with brine, dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customto afford a moist solid
  6. temperatureheated
  7. temperatureto reflux
  8. temperatureto cool to room temperature
  9. filtrationfiltered (repeated three times)

출처 및 근거

ORD 기록
ord-0ec59d321b824d4aa36ef231c649cb12
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921547B2

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