Hydrochloric Acid → 3-(aminomethyl)-4-butoxy-2-isobutyl-6-[(E)-2-(1,3-thiazol-4-yl-)ethenyl]-1(2H)-isoquinolinone hydrochloride

HRID 1797736Notes

Reaction equation

HRID 1797736 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[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15](/[CH:24]=[CH:25]/[C:26]1[N:27]=[CH:28][S:29][CH:30]=1)=[CH:14][CH:13]=2)(C)(C)C.[ClH:37]>C(OCC)(=O)C>[ClH:37].[NH2:7][CH2:8][C:9]1[N:10]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:11](=[O:31])[C:12]2[C:17]([C:18]=1[O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:16][C:15](/[CH:24]=[CH:25]/[C:26]1[N:27]=[CH:28][S:29][CH:30]=1)=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22175662Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate

Product 1

HCID 221753443-(aminomethyl)-4-butoxy-2-isobutyl-6-[(E)-2-(1,3-thiazol-4-yl-)ethenyl]-1(2H)-isoquinolinone hydrochlorideYield 84.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl{4-butoxy-2-isobutyl-1-oxo-6-[(E)-2-(1,3-thiazol-4-yl)ethenyl]-1,2-dihydro-3-isoquinolinyl}methylcarbamate (0.16 g, 0.3 mmol) was dissolved in a solution of 4N hydrogen chloride in ethyl acetate solution (5 ml). The solution was stirred at room temperature for 1 h. The reaction was concentrated under reduced pressure, and the residue was recrystallized from methanol-diisopropyl ether to give 3-(aminomethyl)-4-butoxy-2-isobutyl-6-[(E)-2-(1,3-thiazol-4-yl-)ethenyl]-1(2H)-isoquinolinone hydrochloride (0.11 g, 84.6%) as crystals.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-934417b91dd148e68da1c47860bb1e14
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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