Water → HCID 178515267, 화합물

HRID 654599노트

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HRID 654599 반응식
[C:1]1([C:7]2[C:8]([NH2:12])=[N:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]1([N:19]2[C:23](=[O:24])[C:22](=O)[CH:21]([C:26](OCC)=[O:27])[CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(O)(=O)C.C(O)C>[CH:13]1([N:19]2[CH2:20][C:21]3[C:26](=[O:27])[N:9]4[N:10]=[CH:11][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[C:8]4[NH:12][C:22]=3[C:23]2=[O:24])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

6

반응물 3

HCID 962WaterHCID 28188294-Carbethoxy-1-cyclohexyl-2,3-dioxopyrrolidineHCID 178509246HCID 178509246, 화합물

생성물 1

HCID 178515267HCID 178515267, 화합물수율 51%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

4-Phenylpyrazol-3-amine [Anderson, E. L. et al., "Synthesis . . . 3-Amino-4-Arylpyrazoles", J. Med. Chem., 7, (1964), pp. 259-268] (3.00 g, 18.8 mmole) and ethyl 1-cyclohexyl-4,5-dioxo-3-pyrrolidinecarboxylate (4.77 g, 18.8 mmole) were combined in glacial acetic acid (19 mL) and stirred under reflux for five hours. No precipitate was observed throughout the course of the reaction. Upon cooling, the reaction solidified to a light yellow mass which was dissolved in 95% ethanol (100 mL) at reflux and water (50 mL) was added slowly while maintaining reflux. After cooling to room temperature, the thick yellow solid was collected by suction filtration and washed with more ethanol/water. Drying under vacuum left 5.37 g homogenous by TLC. Unsatisfactory analysis prompted recrystallization from 95% ethanol (200 mL) to give 3.31 g (m.p.>148°, dec.). Yield: 51% of the subtitled compound. 1H NMR CDCl3, δ) 8.08 (s, 1H, pyrazole-H), 7.44 (d, 2H, J=8 Hz, 2-phenyl H), 7.36 (t, 2H, J=8 Hz, 3-phenyl H), 7.23 (t, 1H, J=8 Hz, 4-phenyl H), 4.37 (s, 2H, lactam CH2), 3.99 (m, 1H, cyclohexyl CH), 1.1-1.9 (m, 10H, chclohexyl CH2); IR (mull) 3519, 1692, 1638, 1613, 1455 cm-1 ; UV (ethanol) λmax(ε) 205 (29,400), 210sh (27,750), 237 (18,350), 268 (18,760), 370 (7700); MS m/e (rel. intens.) 349 (M+1, 23), 348 (M+, 97), 267 (18), 266 (100), 210 (8), 183 (9); Exact mass calc'd for C20H20N4O2 =348.1586; Found=348.1593; TLC (silica, 10% methanol/chloroform) Rf 0.52.

후처리

  1. customet al., "Synthesis
  2. temperatureunder reflux for five hours
  3. customNo precipitate was observed throughout the course of the reaction
  4. temperatureUpon cooling
  5. temperatureat reflux
  6. temperaturewhile maintaining
  7. temperaturereflux
  8. filtrationthe thick yellow solid was collected by suction filtration
  9. washwashed with more ethanol/water
  10. customDrying under vacuum
  11. waitleft 5.37 g homogenous by TLC
  12. customrecrystallization from 95% ethanol (200 mL)
  13. customto give 3.31 g (m.p.>148°, dec.)

출처 및 근거

ORD 기록
ord-071c5195e52847a8aed773b344176d5f
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05132424

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