Methanol → 2-Furan-2-yl-6-(3-phenyl-3-phenylamino-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

HRID 2242914노트

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HRID 2242914 반응식
[CH:1](=[N:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.CO.[C:22]([C:24]1[N:25]=[C:26]([NH2:38])[C:27]2[N:28]([N:30]=[C:31]([C:33]3[O:34][CH:35]=[CH:36][CH:37]=3)[N:32]=2)[CH:29]=1)#[CH:23]>O>[O:34]1[CH:35]=[CH:36][CH:37]=[C:33]1[C:31]1[N:32]=[C:27]2[C:26]([NH2:38])=[N:25][C:24]([C:22]#[C:23][CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:29][N:28]2[N:30]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 10858N-BenzylideneanilineHCID 866099456-Ethynyl-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

생성물 1

HCID 685461232-Furan-2-yl-6-(3-phenyl-3-phenylamino-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

시약·촉매·용매 1

HCID 962Water용매

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온도
40 °C

실험 절차

To a solution of benzylidene-phenyl-amine (0.05 mmol) (prepared by heating neat phenylamine (0.05 mmol) and benzaldehyde (0.05 mmol) at 60° C. for 2 hours) in a 1:1 mixture of THF (250 uL) and methanol (250 uL) was added the above 6-ethynyl-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (11 mg, 0.05 mmol). CuBr (2.2 mg, 0.015 mmol, 30 mol %) was added to the reaction mixture followed by RuCl3 (0.03 mg, 0.0015, 3 mol %) in water (50 μL). The reaction vessel was degassed and heated at 40° C., for 18 hours. After cooling, water was added and the residue was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, and concentrated in vacuo to yield a crude product, which was purified using preparative HPLC to afford 2-furan-2-yl-6-(3-phenyl-3-phenylamino-prop-1-ynyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine. 1H NMR (300 MHz, Acetone-d6) δ 8.20 (s, 1H), 7.79-7.71 (3H), 7.43-7.40(3H), 7.15-7.11(4H), 6.90-6.87(2H), 6.67-6.65 (2H), 5.70 (s, 1H), 2.55(s, 1H). MS: m/z 407 [M+1].

후처리

  1. customThe reaction vessel was degassed
  2. temperatureAfter cooling
  3. additionwater was added
  4. extractionthe residue was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield a crude product, which
  8. customwas purified

출처 및 근거

ORD 기록
ord-4aa381a3b89344f8ba81dd1e4f4d3b62
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674791B2

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