Hydrochloric Acid → (1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(3,4-dihydro-1H-isoquinolin-2-yl)-methanone

HRID 14630

Reaction equation

HRID 14630 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]([C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])=[CH:11][N:10]=1)(C)(C)C.Cl>CCOC(C)=O>[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]([C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59341075[4-(3,4-Dihydro-1H-isoquinoline-2-carbonyl)-6,8-dimethoxy-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 46846828(1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-(3,4-dihydro-1H-isoquinolin-2-yl)-methanoneYield 116.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of [4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)-6,8-dimethoxy-isoquinolin-1-ylmethyl]-carbamic acid tert-butyl ester (79 mg, 0.17 mmol) in 3 mL of EtOAc was stirred at room temperature, and 2 mL of HCl (3.2 M in EtOAc) was added. After stirring at room temperature overnight (deprotection is typically complete after 4-8 hours) the solvent was removed under reduced pressure and the residue was triturated with ether to give 75 mg of product as the HCl salt. H1-NMR (DMSO): δ, 8.42 (br s, 1H), 7.18 (m, 4H), 6.60 (m, 2H), 4.65 (br s, 2H), 4.27 (m, 2H), 3.98 (br s, 3H), 3.80 (s, 3H), 3.39 (m, 3H), 3.86 (m, 2H), [Note: Rotamers observed.] MS: APCI (M+H) calc'd for C22H23N3O3+H 378.4; found 378.2.

Workup

  1. waitis typically complete after 4-8 hours
  2. custom) the solvent was removed under reduced pressure
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-9989403347504be7822a58ed50466fdf
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Linked notes

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