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

HRID 14670Notes

Reaction equation

HRID 14670 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]([CH3:29])[N:28]=2)=[CH:11][N:10]=1)(C)(C)C.[ClH:31]>C(Cl)Cl.O1CCOCC1>[ClH:31].[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]([CH3:29])[N:28]=2)=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59341106[6,7-Dimethoxy-4-(4-methyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

Product 1

HCID 86761127(1-Aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-(4-methyl-thiazol-2-yl)amine hydrochloride saltYield 75%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

[6,7-Dimethoxy-4-(4-methyl-thiazol-2-ylamino)-isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester (11.6 mg, 0.0269 mmol) in CH2Cl2 (0.6 mL) was added a 4.0 M HCl solution in dioxane (0.40 mL) at room temp. After the reaction mixture was stirred at room temperature for 5.0 h, the suspension was filtered. The yellow solid was further dried in vacuo to give (1-aminomethyl-6,7-dimethoxy-isoquinolin-4-yl)-(4-methyl-thiazol-2-yl)amine hydrochloride salt (7.4 mg; 75%). 1H-NMR (D2O): δ, 8.33 (s, 1H), 7.26 (s, 1H), 7.15 (s, 1H), 6.34 (s, 1H), 4.70 (s, 2H), 3.88 (s, 3H), 3.81 (s, 3H), 2.05 (s, 3H); MS: calculated for C16H19N4O2S (M−Cl) 331.0; found: 331.0.

Workup

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

Sources & evidence

ORD record
ord-6e2250b36bbb4244b003a6093448cee3
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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