Ethylenediamine → 7-((4-methoxybenzyl)oxy)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,8(2H)-dione

HRID 525854Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:18])[CH:11]=[C:12]([C:15]([OH:17])=O)O[CH:14]=2)=[CH:5][CH:4]=1.[CH2:21]([NH2:24])[CH2:22][NH2:23]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:18])[CH:11]=[C:12]3[C:15](=[O:17])[NH:24][CH2:21][CH2:22][N:23]3[CH:14]=2)=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

The mixture of 5-((4-methoxybenzyl)oxy)-4-oxo-4H-pyran-2-carboxylic acid (Example 2b) (5.24 g, 18.21 mmol), ethane-1,2-diamine (1.830 mL, 27.3 mmol) in water (80 mL) was stirred at 60° C. for 1 h and then 80° C. for 20 h. Yellow solid precipitated from the reaction when heating. After cooling, white precipitate was filtered off, washed with 20 mL of cold water/acetone (v:v=1:1) and dried to give 7-((4-methoxybenzyl)oxy)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,8(2H)-dione (4.15 g, 13.82 mmol, 76% yield) as white solid, which was used in the next step without further purification. LCMS (M+H)+: 301.2

Workup

wait80° C. for 20 h
customYellow solid precipitated from the reaction when
temperatureheating
temperatureAfter cooling
filtrationwhite precipitate was filtered off
washwashed with 20 mL of cold water/acetone (v:v=1:1)
customdried

Sources & evidence

ORD record: ord-01343c6a2b26435580625fcf406cebd3
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340556B2

Reaction notes

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