4-Methoxybenzylamine → 6-(4-methoxybenzyl)-3-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533162Notes

Reaction equation

[CH:1]([C:3]1[N:12]=[CH:11][C:10]([CH:13]=[CH2:14])=[CH:9][C:4]=1[C:5]([O:7]C)=O)=[CH2:2].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][NH2:22])=[CH:19][CH:18]=1>CC(N(C)C)=O>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:22]2[CH2:2][CH2:1][C:3]3[N:12]=[CH:11][C:10]([CH:13]=[CH2:14])=[CH:9][C:4]=3[C:5]2=[O:7])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Methyl 2,5-divinylnicotinate (2.1 g, 11.1 mmol) was combined with p-methoxybenzylamine (2 mL, 15 mmol) and dimethylacetamide (7 mL) and heated for 20 min in a microwave reactor at 150° C. The reaction mixture was concentrated and purified over silica gel (0-100% EtOAc/hexanes) using automated chromatography. The product containing fractions were combined and evaporated under reduced pressure to give the compound (2.99 g, 92%). LC-MS (M+H)=295.1.

Workup

concentrationThe reaction mixture was concentrated
custompurified over silica gel (0-100% EtOAc/hexanes)
additionThe product containing fractions
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-ae011d635ee54892ab279714c536943e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853237B2

Reaction notes

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