Methyl[5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate → Methyl 2-[2-[(3-chlorophenyl)methyl]-9-hydroxy-1,8-dioxo-pyrido[1,2-a]pyrazin-7-yl]acetate

HRID 1349483Notes

Reaction equation

C([O:8][C:9]1[C:10](=[O:37])[C:11]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:12][N:13]([CH2:26][CH:27](OC)OC)[C:14]=1[C:15](=[O:25])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:16]1[CH:27]=[CH:26][N:13]2[CH:12]=[C:11]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:10](=[O:37])[C:9]([OH:8])=[C:14]2[C:15]1=[O:25]

Participants

Conditions

Temperature: 70 °C

Procedure

Methyl [5-benzyloxy-6-(3-chlorobenzylcarbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridin-3-yl]acetate (30 mg) was dissolved in trifluoroacetic acid (1 ml) and the mixture was stirred at 70° C. for 4 hr. The mixture was cooled and concentrated. Toluene was added to the residue and the mixture was concentrated again, which operations were performed twice. Crystallization from ethyl acetate-diisopropyl ether gave methyl [2-(3-chlorobenzyl)-9-hydroxy-1,8-dioxo-1,8-dihydro-2H-pyrido[1,2-a]pyrazin-7-yl]acetate (17 mg).

Workup

temperatureThe mixture was cooled
concentrationconcentrated
additionToluene was added to the residue
concentrationthe mixture was concentrated again
customCrystallization from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-aab95231e85e43d8ae8df371b2ad395c
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211572B2

Reaction notes

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