Hydrochloric Acid → HCID 22175367, compound

HRID 1797537Notes

Reaction equation

HRID 1797537 reaction equation
[CH2:1]([O:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:7]1(/C=C/C(N)=O)[CH2:21][NH:22]C(OC(C)(C)C)=O)[CH2:2][CH2:3][CH3:4].[ClH:35]>C(OCC)(=O)C>[ClH:35].[NH2:22][CH2:21][C:7]1[N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:9](=[O:16])[C:10]2[C:15]([C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][C:13](/[CH:11]=[CH:10]/[C:9]([NH2:8])=[O:16])=[CH:12][CH:11]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22176290HCID 22176290, compound

Product 1

HCID 22175367HCID 22175367, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (E)-3-(4-butoxy-3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)-2-propenamide (0.14 g, 0.3 mmol) in ethyl acetate (5 mL) was added a solution of 4N hydrogen chloride in ethyl acetate (5 mL) and the obtained solution was stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure, and the precipitated crystals were recrystallized from methanol-diisopropyl ether to give (E)-3-[3-(aminomethyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-2-propenamide hydrochloride (0.11 g, 91.7%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe precipitated crystals were recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-1789ff1f2ba3454098e9a1cb66bd9354
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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