Hydrochloric Acid → 1-Aminomethyl-6,7-dimethoxy-isoquinoline-4-carboxylic acid (2-methoxy-ethyl)-amide

HRID 14656Notes

Reaction equation

HRID 14656 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]([C:23](=[O:29])[NH:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:11][N:10]=1)(C)(C)C.Cl.C(OCC)C>O1CCOCC1>[CH3:28][O:27][CH2:26][CH2:25][NH:24][C:23]([C:12]1[C:13]2[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[C:9]([CH2:8][NH2:7])=[N:10][CH:11]=1)=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 68613466[6,7-Dimethoxy-4-(2-methoxy-ethylcarbamoyl)-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 468471641-Aminomethyl-6,7-dimethoxy-isoquinoline-4-carboxylic acid (2-methoxy-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of [6,7-dimethoxy-4-(2-methoxy-ethylcarbamoyl)-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester (45 mg, 0.11 mmol) in dioxane (2 ml) was treated with 4M HCl in dioxane (2 ml) and the mixture was stirred overnight at room temperature. Diethyl ether was added and the HCl salt was collected by suction filtration (38 mg, quant.): 1H NMR (DMSO-d6) δ 3.28 (s, 3H), 3.47-3.53 (m, 4H), 3.89 (s, 3H), 3.99 (s, 3H), 4.72 (m, 2H), 7.46 (s, 1H), 7.70 (s, 1H), 8.42 (s, 1H), 8.65 (br s, 3H), 8.82 (m, 1H); MS (APCI) m/z 320.1 [M+1]+.

Workup

  1. filtrationthe HCl salt was collected by suction filtration (38 mg, quant.)

Sources & evidence

ORD record
ord-efc9d7f09fad4dff9ac7432c2e101b23
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Reaction notes

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