Diisopropylethylamine → HCID 71212232, 화합물

HRID 1752259노트

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HRID 1752259 반응식
Cl[C:2]1[N:7]=[N:6][CH:5]=[C:4]2[O:8][CH2:9][CH2:10][CH2:11][C:3]=12.C(N(CC)C(C)C)(C)C.[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH2:26]>C(O)(C)C>[CH3:21][O:22][C:23]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:24]=1[CH2:25][NH:26][C:2]1[N:7]=[N:6][CH:5]=[C:4]2[O:8][CH2:9][CH2:10][CH2:11][C:3]=12

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5972502,4-Dimethoxybenzylamine2회HCID 89375780HCID 89375780, 화합물

생성물 1

HCID 71212232HCID 71212232, 화합물수율 60%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
115 °C

실험 절차

A mixture of 5-chloro-3,4-dihydro-2H-pyrano[2,3-d]pyridazine (150 mg, 0.879 mmol), N,N-diisopropylethylamine (0.154 mL, 114 mg, 0.879 mmol), and 2,4-dimethoxybenzylamine (294 mg, 1.76 mmol) in isopropanol (2 mL) was heated in a sealed tube 18 hours at 115° C. and then 4.5 hours at 145° C. before addition of excess 2,4-dimethoxybenzylamine (about 2 g, 12 mmol). The reaction was stirred at 145° C. for 18 hours. After cooling to room temperature, isopropanol was removed in vacuo. The crude was then treated with diethyl ether (30 mL). A tan solid was removed by filtration. The filtrate was washed twice with small amounts of saturated aqueous ammonium chloride. The organic layer was dried over sodium sulfate, filtered, and concentrated down. The crude was purified by silica gel chromatography with a 0 to 10% methanol/dichloromethane gradient to afford the title compound (159 mg) as an amber foamy oil. MS (ESI) [m/e, (M)+]=301.8. 1H NMR (400 MHz, chloroform-d) δ ppm 8.22 (s, 1H), 7.35 (d, J=8.08 Hz, 1H), 6.36-6.56 (m, 2H), 4.73 (d, J=5.56 Hz, 2H), 4.37-4.56 (m, 1H), 4.11-4.24 (m, 2H), 3.86 (s, 3H), 3.81 (s, 3H), 2.27-2.31 (m, 2H), 2.04-2.11 (m, 2H).

후처리

  1. temperatureAfter cooling to room temperature
  2. customisopropanol was removed in vacuo
  3. additionThe crude was then treated with diethyl ether (30 mL)
  4. customA tan solid was removed by filtration
  5. washThe filtrate was washed twice with small amounts of saturated aqueous ammonium chloride
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated down
  9. customThe crude was purified by silica gel chromatography with a 0 to 10% methanol/dichloromethane gradient

출처 및 근거

ORD 기록
ord-752e5d075fc04e17ad8180f715d21a13
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163003B2

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