Hydrochloric Acid → 2-(1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-ylamino)thiazole-4-carboxylic acid ethyl ester hydrochloride salt

HRID 14651Notes

Reaction equation

HRID 14651 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]2[C:21]3[C:16](=[C:17]([O:24][CH3:25])[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[C:15]([CH2:26][NH:27]C(OC(C)(C)C)=O)=[N:14][CH:13]=2)[S:9][CH:10]=1)=[O:5])[CH3:2].[ClH:35]>C(Cl)Cl.O1CCOCC1>[ClH:35].[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]2[C:21]3[C:16](=[C:17]([O:24][CH3:25])[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=3)[C:15]([CH2:26][NH2:27])=[N:14][CH:13]=2)[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 593411092-[1-(Tert-butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinolin-4-ylamino]thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 867611252-(1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-ylamino)thiazole-4-carboxylic acid ethyl ester hydrochloride saltYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

2-[1-(tert-Butoxycarbonylamino-methyl)-6,8-dimethoxy-isoquinolin-4-ylamino]thiazole-4-carboxylic acid ethyl ester (22 mg, 0.045 mmol) in CH2Cl2 (1.0 mL) was added a 4.0 M HCl solution in dioxane (0.67 mL) at room temp. After the reaction mixture was stirred at room temperature for 4.5 h, the suspension was filtered. The yellow solid was dried in vacuo to give 2-(1-aminomethyl-6,8-dimethoxy-isoquinolin-4-ylamino)thiazole-4-carboxylic acid ethyl ester hydrochloride salt (14.0 mg; 73% yield). 1H-NMR (D2O): δ, 8.84 (d, 1H, J=6.3 Hz), 7.70 (s, 1H), 6.92 (s, 1H), 6.77 (s, 1H), 4.66 (s, 2H), 4.20 (q, 2H, J=7.1 Hz), 3.92 (s, 3H), 3.84 (s, 3H), 1.20 (t, 3H, J=7.3 Hz); MS: calculated for C18H21N4O4S (M−Cl) 389.0; found: 389.0.

Workup

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

Sources & evidence

ORD record
ord-109d855e41924ad6915c79498e8df39c
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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