Hydrochloric Acid → HCID 135788476, compound

HRID 1797676Notes

Reaction equation

HRID 1797676 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:16][C:15]([C:25]1[NH:29][C:28](=[O:30])[O:27][N:26]=1)=[CH:14][CH:13]=2)(C)(C)C.[ClH:37]>C(O)C.C(OCC)(=O)C>[ClH:37].[NH2:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[CH:16][C:15]([C:25]1[NH:29][C:28](=[O:30])[O:27][N:26]=1)=[CH:14][CH:13]=2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136376437HCID 136376437, compound

Product 1

HCID 135788476HCID 135788476, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl[2-isobutyl-1-oxo-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.18 g, 0.37 mmol) was dissolved in ethanol (4 ml) and a solution (4 ml) of 4N hydrogen chloride in ethyl acetate was added. The mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was washed with diisopropyl ether (2 ml) and recrystallized from ethyl acetate-ethanol (20:1) to give 3-(aminomethyl)-2-isobutyl-6-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)-4-phenyl-1(2H)-isoquinolinone hydrochloride (0.12 g, 80%) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with diisopropyl ether (2 ml)
  3. customrecrystallized from ethyl acetate-ethanol (20:1)

Sources & evidence

ORD record
ord-65fcc920f1894efa8587884f89ff7ca6
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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