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 1034959Notes

Reaction equation

HRID 1034959 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-84e1f6bee5514cb5bfe487cd961a6fc0
Source dataset
uspto-grants-2013_10
Patent number
US08546368B2

Reaction notes

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