Hydrochloric Acid → 2-(1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-N-(4-methoxy-benzyl)-acetamide

HRID 14675Notes

Reaction equation

HRID 14675 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([CH2:23][C:24](=[O:35])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:11][N:10]=1)(C)(C)C.Cl.CCO>CCOC(C)=O.O1CCOCC1>[NH2:7][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[C:12]([CH2:23][C:24]([NH:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)=[O:35])=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 59341099{6,7-Dimethoxy-4-[(4-methoxy-benzylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 468473662-(1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-N-(4-methoxy-benzyl)-acetamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of {6,7-dimethoxy-4-[(4-methoxy-benzylcarbamoyl)-methyl]-isoquinolin-1-ylmethyl}-carbamic acid tert-butyl ester (64 mg, 0.13 mmol) in 1.5 mL of EtOAc was added 3 mL of a 4 M solution of HCl in dioxane. After stirring at room temperature for 1 h, 1 mL of EtOH was added to facilitate solution. The reaction was stirred for 48 hours and the precipitated HCl salt was collected by filtration (58 mg, >100%). H1-NMR (DMSO): 9.00 (m, 1H), 8.79 (br s, 3H), 8.35 (s, 1H), 7.62 (s, 1H), 7.46 (s, 1H), 7.12 (d, J=8.5 Hz, 2H), 6.80 (d, 2H, J=8.3 Hz), 4.75 (br s, 2H), 4.18 (d, J=5.4 Hz, 2H), 4.02 (s, 3H), 4.00 (s, 2H), 3.82 and 3.68 (s, 3H); MS: APCI (M+H) calc'd for C22H25N3O4+H 396.5; found 396.2.

Workup

  1. stirringThe reaction was stirred for 48 hours
  2. filtrationthe precipitated HCl salt was collected by filtration (58 mg, >100%)

Sources & evidence

ORD record
ord-455031f713684cdfab41334db899b726
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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