Hydrochloric Acid → 4-aminomethyl-1-phenyl-1H-pyridin-2-one

HRID 2236883Notes

Reaction equation

HRID 2236883 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9]C(=O)OC(C)(C)C)[CH:5]=[CH:4][N:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O1CCOCC1>[NH2:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:2](=[O:1])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 42625677Tert-butyl (2-oxo-1-phenyl-1,2-dihydropyridin-4-ylmethyl)-carbamate

Product 1

HCID 426256794-aminomethyl-1-phenyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl (2-oxo-1-phenyl-1,2-dihydropyridin-4-ylmethyl)-carbamate (83 mg, 0.28 mmol) is treated with 4N hydrogen chloride in dioxane in order to remove the Boc protecting group. The hydrochloride salt of 4-aminomethyl-1-phenyl-1H-pyridin-2-one, obtained after concentration of the reaction mixture, is dissolved in N,N-dimethylformamide (5 mL) and is coupled to (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (92 mg, 0.28 mmol) in the presence of triethylamine (200 μL). After one hour, the reaction mixture is concentrated under reduced pressure and purified by flash silica gel chromatography (methanol/chloroform) to provide (4Z)-6-iodo-4-({[(2-oxo-1-phenyl-1,2dihydropyridin-4-yl)methyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione as a pale yellow solid (8.8 mg, 6.3%).

Workup

  1. customto remove the Boc protecting group

Sources & evidence

ORD record
ord-bd847cd41b054f73b0690895fd42bbc2
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

Loading…