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 1034959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034959
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-84e1f6bee5514cb5bfe487cd961a6fc0
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546368B2

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