Hydrochloric Acid → 4-aminomethyl-1-furan-3-yl-1H-pyridin-2-one

HRID 2236889Notes

Reaction equation

HRID 2236889 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([N:6]2[CH:11]=[CH:10][C:9]([CH2:12][NH:13]C(=O)OC(C)(C)C)=[CH:8][C:7]2=[O:21])=[CH:2]1.Cl>O1CCOCC1>[NH2:13][CH2:12][C:9]1[CH:10]=[CH:11][N:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)[C:7](=[O:21])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 42625749Tert-butyl (1-furan-3-yl-2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-carbamate

Product 1

HCID 426257514-aminomethyl-1-furan-3-yl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (1-furan-3-yl-2-oxo-1,2-dihydro-pyridin-4-ylmethyl)-carbamate (0.18 g, 0.62 mmol) is treated with 4N hydrogen chloride in dioxane in order to remove the Boc protecting group. The hydrochloride salt of 4-aminomethyl-1-furan-3-yl-1H-pyridin-2-one, obtained after concentration of the reaction mixture, is dissolved in N,N-dimethylformamide (4 mL) and is coupled to (4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (0.20 g, 0.62 mmol) in the presence of triethylamine (400 μL). After three hours, the reaction mixture is concentrated under reduced pressure, and the residue is triturated with acetonitrile to provide (4Z)-4-[({[1-(3-furyl)-2-oxo-1,2-dihydropyridin-4-yl]methyl}amino)methylene]-6-iodoisoquinoline-1,3(2H,4H)-dione as a brown powder (0.12 g, 40%).

Workup

  1. customto remove the Boc protecting group

Sources & evidence

ORD record
ord-bdf5c057664649049d3971fb3858cb2f
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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