Hydrogen chloride-ethyl acetate → HCID 22175515, compound

HRID 1797750Notes

Reaction equation

HRID 1797750 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[O:26][C:27]([CH3:30])=[N:28][N:29]=1)=[CH:14][CH:13]=2)(C)(C)C.C(OC(=O)C)C.Cl>C(=O)([O-])O.[Na+]>[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[O:26][C:27]([CH3:30])=[N:28][N:29]=1)=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 22175906HCID 22175906, compound

Product 1

HCID 22175515HCID 22175515, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of tert-butyl[2-isobutyl-6-(5-methyl-1,3,4-oxadiazol-2-yl)-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.20 g, 0.41 mmol) and 4N hydrogen chloride ethyl acetate solution (4 mL) was stirred for 17 h at room temperature. The reaction mixture was concentrated, the residue was washed with diisopropyl ether (5 mL×2) to give a pale yellow powder. The powder was added to aqueous saturated sodium hydrogencarbonate (30 mL), the resulting mixture was extracted with ethyl acetate-tetrahydrofuran (1:1, v/v, 50 mL×2). The organic layers were combined, washed with brine (25 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1 (v/v)) and recrystallized from n-hexane-ethyl acetate to give 3-(aminomethyl)-2-isobutyl-6-(5-methyl-1,3,4-oxadiazol-2-yl)-4-phenyl-1(2H)-isoquinolinone (0.11 g, 72%) as pale yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with diisopropyl ether (5 mL×2)
  3. customto give a pale yellow powder
  4. extractionthe resulting mixture was extracted with ethyl acetate-tetrahydrofuran (1:1, v/v, 50 mL×2)
  5. washwashed with brine (25 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1 (v/v))
  9. customrecrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-6d929914fa0c467f9b6cb65053022d13
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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