Hydrochloric Acid → (1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-(4-phenyl-thiazol-2-yl)amine hydrochloride salt

HRID 14668

Reaction equation

HRID 14668 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]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=2)=[CH:11][N:10]=1)(C)(C)C.[ClH:36]>C(Cl)Cl.O1CCOCC1>[ClH:36].[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]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:28]=2)=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59341076[6,7-Dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

Product 1

HCID 86761126(1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-(4-phenyl-thiazol-2-yl)amine hydrochloride saltYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

[6,7-Dimethoxy-4-(4-phenyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester (44 mg, 0.0853 mmol) in CH2Cl2 (1 mL) was added a 4.0 M HCl solution in dioxane (0.21 mL) at room temp. After the reaction mixture was stirred at room temperature for 21 h, the suspension was filtered. The yellow solid was further dried in vacuo to give (1-aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-(4-phenyl-thiazol-2-yl)amine hydrochloride salt (26.1 mg; 71%). 1H-NMR (D2O): δ, 8.82 (s, 1H), 7.09-7.00 (m, 6H), 6.69 (s, 1H), 6.51 (s, 1H), 4.43 (s, 2H), 3.70 (s, 3H), 3.59 (s, 3H); MS: calculated for C21H21N4O2S (M−Cl) 393.0; found: 393.0.

Workup

  1. filtrationthe suspension was filtered
  2. customThe yellow solid was further dried in vacuo

Sources & evidence

ORD record
ord-6300e10c0604458b8044bd05688864b0
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Linked notes

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