Hydrochloric Acid → 3-(1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-1-benzyl-1-methyl-urea

HRID 14663Notes

Reaction equation

HRID 14663 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]([NH:23][C:24]([N:26]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:27])=[O:25])=[CH:11][N:10]=1)(C)(C)C.Cl>CCOC(C)=O>[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]([NH:23][C:24](=[O:25])[N:26]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH3:27])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59341092[4-(3-Benzyl-3-methyl-ureido)-6,7-dimethoxy-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 468471703-(1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-1-benzyl-1-methyl-ureaYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of the Boc protected amine, [4-(3-benzyl-3-methyl-ureido)-6,7-dimethoxy-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester, (155 mg) was taken up in 5 mL of EtOAc, then 600 μL of HCl in EtOAc was added and the reaction was allowed to stir overnight. Solvent was removed in vacuo, and the resulting white solid was washed with ether to give 109 mg (89%) of the desired product as the hydrochloride salt. H1-NMR (CDCl3): δ 8.31 (s, 1H), 7.3-7.4 (m, 5H), 7.17 (s, 1H), 6.82 (s, 1H), 6.51 (s, 1H), 4.66 (s, 2H), 4.29 (s, 2H), 3.99 (s, 3H), 3.83 (s, 3H), 3.16 (s, 3H), 2.83 (br s, 1H). MS: APCI (M+H) calc'd for C26H32N4O5+H 481.6; found 481.0.

Workup

  1. customSolvent was removed in vacuo
  2. washthe resulting white solid was washed with ether

Sources & evidence

ORD record
ord-b7fb7bf9baf6432b847a7ecbbc9aee74
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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