Hydrochloric Acid → (1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(4-methyl-thiazol-2-yl)amine hydrochloride salt

HRID 14649Notes

Reaction equation

HRID 14649 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])=[CH:16][C:17]=2[O:19][CH3:20])[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])=[CH:16][C:17]=2[O:19][CH3:20])[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 59341088[6,8-Dimethoxy-4-(4-methyl-thiazol-2-ylamino)isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester

Product 1

HCID 86761124(1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(4-methyl-thiazol-2-yl)amine hydrochloride saltYield 53%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of [6,8-dimethoxy-4-(4-methyl-thiazol-2-ylamino)-isoquinolin-1-ylmethyl]carbamic acid tert-butyl ester (20 mg, 0.045 mmol) in 1 mL CH2Cl2 was added a 4.0 M HCl solution in dioxane (0.70 mL). After the reaction mixture was stirred at room temperature for 20 h, the resulting yellow solid was collected by suction filtration, and dried in vacuo to give (1-aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(4-methyl-thiazol-2-yl)amine hydrochloride salt (9.0 mg, 53%). 1H-NMR (D2O): δ, 8.35 (s, 1H), 6.75 (s, 2H), 6.35 (s, 1H), 4.78 (s, 2H), 3.89 (s, 3H), 3.77 (s, 3H), 2.06 (s, 3H); MS: calculated for C16H19N4O2S (M−Cl) 331.0; found: 331.0.

Workup

  1. filtrationthe resulting yellow solid was collected by suction filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-2ca6f445148942d78e2b1b6695a4ce0c
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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