Ethyl isocyanate → Benzyl 3-(3-methyl-5-oxo-4,5,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-1-yl)-pyrrolidine-1-carboxylate

HRID 1034959노트

반응식

HRID 1034959 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9]2)[C:3]=1[C:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1.C(N=[C:32]=[O:33])C>N1C=CC=CC=1>[CH3:7][N:6]1[C:2]2[NH:1][C:32](=[O:33])[C:24]3[CH2:25][CH2:26][CH2:27][CH2:28][C:23]=3[C:3]=2[C:4]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9]2)=[N:5]1

참가 물질

4

반응물 2

HCID 8022Ethyl isocyanateHCID 69162390benzyl 3-(5-amino-4-cyclohex-1-enyl-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate

생성물 1

HCID 136353285Benzyl 3-(3-methyl-5-oxo-4,5,6,7,8,9-hexahydropyrazolo[3,4-c]isoquinolin-1-yl)-pyrrolidine-1-carboxylate수율 77%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a stirring solution of EXAMPLE 24D (0.967 g, 2.54 mmol) in pyridine (10 mL) was added ethyl isocyanate (0.6 mL, 7.62 mmol) and the solution heated at reflux for 24 hours. After cooling, the mixture was concentrated and the residue recrystallized from methanol. The white solid was collected by filtration, washed with methanol and dried to give the title compound (794 mg, 77%). 1H NMR (DMSO-d6): 1.66-1.77 (m, 4H), 2.01-2.17 (m, 1H), 2.18-2.27 (m, 1H), 2.37-2.43 (m, 2H), 2.86-2.92 (m, 2H), 3.33-3.46 (m, 1H), 3.49-3.64 (m, 2H), 3.68-3.76 (m, 1H), 3.76 (s, 3H), 3.77-3.85 (m, 1H), 5.08 (s, 2H), 7.29-7.35 (m, 1H), 7.34-7.39 (m, 5H).

후처리

  1. temperaturethe solution heated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated
  5. customthe residue recrystallized from methanol
  6. filtrationThe white solid was collected by filtration
  7. washwashed with methanol
  8. customdried

출처 및 근거

ORD 기록
ord-84e1f6bee5514cb5bfe487cd961a6fc0
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546368B2

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