Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoate → Ethyl 1-(1-methylethyl)-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476081

반응식

HRID 476081 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11](=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.[CH3:19][CH:20]([N:22]1[C:26]([NH2:27])=[CH:25][CH:24]=[N:23]1)[CH3:21]>C1C=CC=CC=1>[CH3:19][CH:20]([N:22]1[C:26]2[N:27]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:25]=2[CH:24]=[N:23]1)[CH3:21]

참가 물질

4

반응물 2

HCID 287267Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoateHCID 10903411-(propan-2-yl)-1H-pyrazol-5-amine

생성물 1

HCID 67124614Ethyl 1-(1-methylethyl)-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate수율 65.1%

시약·촉매·용매 1

HCID 241Benzene용매

반응 조건

온도
62 °C

실험 절차

To a solution of ethyl 4-[4-(methyloxy)phenyl]-2,4-dioxobutanoate (600 mg, 2.397 mmol) in benzene (5 mL) was added 1-(1-methylethyl)-1H-pyrazol-5-amine (300 mg, 2.397 mmol), and the reaction mixture was stirred at 62° C. overnight. The mixture was concentrated in vacuo and the residue was dissolved into acetic acid (3 mL). The solution was stirred at reflux for 1 h and concentrated in vacuo. The residue was purified using column chromatography (Silica gel, 0 to 100% EtOAc/hexanes) to give 530 mg (65%) of product. LCMS E-S (M+H)=340.1 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47-1.57 (m, 3H), 1.61-1.71 (m, 6H), 3.88-3.96 (s, 3H), 4.55 (q, J=7.2 Hz, 2H), 5.46 (m, 1H), 7.03-7.12 (m, 2H), 8.13-8.25 (m, 3H), 8.36-8.43 (m, 1H).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved into acetic acid (3 mL)
  3. stirringThe solution was stirred
  4. temperatureat reflux for 1 h
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

출처 및 근거

ORD 기록
ord-d9ff0b00a30345438d532d0d44edb931
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637509B2

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