Potassium Carbonate → N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine

HRID 729341노트

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HRID 729341 반응식
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[N:9][N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[N:11]2)=O.[CH:17]1([NH:20][C:21]([NH2:23])=[NH:22])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:17]1([NH:20][C:21]2[N:23]=[C:5]([C:7]3[CH:8]=[N:9][N:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[N:11]4)[CH:4]=[CH:3][N:22]=2)[CH2:19][CH2:18]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 11458585HCID 11458585, 화합물HCID 178512453HCID 178512453, 화합물

생성물 1

HCID 6918710N-cyclopropyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine수율 75%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
165 °C

실험 절차

To a solution of (2E)-3-(dimethylamino)-1-pyrazolo[1,5-b]pyridazin-3-yl-2-propen-1-one (43 mg, 0.20 mmol) in DMF (2 mL) was added N-cyclopropylguanidine.0.5H2SO4 (160 mg, 0.80 mmol) and potassium carbonate (110 mg, 0.80 mmol). The reaction was heated at an oil bath temperature of 165° C. for about 18 hours. The mixture was cooled to RT and the solvent was removed in vacuo. The residue was dissolved in chloroform and filtered. The filtrate was purified by flash column chromatography (0-10% gradient MeOH/CH2Cl2) to give the title compound as a yellow solid (38 mg, 75%). 1H-NMR (400 MHz, d6-DMSO) δ 9.13 (dd, 1H, J=9.0, 1.6 Hz), 8.77 (s, 1H), 8.53 (dd, 1H, J=4.4, 1.6 Hz), 8.24 (d, 1H, J=5.2 Hz), 7.38 (m, 1H), 7.10 (d, 1H, J=5.2 Hz), 2.72 (m, 1H), 0.71 (m, 2H), 0.47 (m, 2H); MS (ESI) (M+H)+ 253.

후처리

  1. temperatureThe mixture was cooled to RT
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in chloroform
  4. filtrationfiltered
  5. customThe filtrate was purified by flash column chromatography (0-10% gradient MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-b23a439e47614ba9a6cc1f5c5cee315f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582630B2

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