Cesium carbonate → HCID 118598864, compound

HRID 1050324Notes

Reaction equation

[Cl:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([C:9]([OH:11])=O)=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:24]=[CH:23][C:17]([CH2:18][NH:19][CH2:20][CH2:21]O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C.O>[Cl:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:21][CH2:20][N:19]([CH2:18][C:17]3[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:24][CH:23]=3)[C:9](=[O:11])[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-chloro-6-oxo-1,6-dihydropyridine-2-carboxylic acid (1, 0.25 g, 1.44 mmol) in acetonitrile (10 mL), 2-((4-methoxybenzyl)amino)ethanol (2, 0.31 g, 1.73 mmol) followed by cesium carbonate (1.18 g, 3.61 mmol) and HATU (1.26 g, 3.32 mmol) were added and the reaction mixture was stirred at 50° C. for 16 h. The reaction mixture was diluted with water and the compound was extracted in ethyl acetate. The organic layer was washed with brine, separated, dried over sodium sulphate and concentrated under reduced pressure. The residue obtained was purified via column chromatography (silica, ethyl acetate/hexanes=60%) to afford 7-chloro-2-(4-methoxybenzyl)-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6-(2H)-dione (3). Yield: 0.24 g, 52%; MS (ESI) m/z 319 [M+1]+.

Workup

additionwere added
extractionthe compound was extracted in ethyl acetate
washThe organic layer was washed with brine
customseparated
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue obtained
customwas purified via column chromatography (silica, ethyl acetate/hexanes=60%)

Sources & evidence

ORD record: ord-7751a359244945f98f995c346ba91bc7
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382248B2

Reaction notes

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