Formaldehyde → HCID 54715338, compound

HRID 2109833Notes

Reaction equation

HRID 2109833 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13](=[O:19])[CH:14]=[C:15]([OH:18])[C:16]([OH:17])=[C:9]3[C:8]2=[O:20])=[CH:4][CH:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[CH2:29]=O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13](=[O:19])[C:14]([CH2:29][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[C:15]([OH:18])[C:16]([OH:17])=[C:9]3[C:8]2=[O:20])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 54723326HCID 54723326, compound

Product 1

HCID 54715338HCID 54715338, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-fluorobenzyl)-8,9-dihydroxy-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione (0.2 g, 0.66 mmol), piperidine (0.13 mL, 1.3 mmol), and formaldehyde (0.08 mL, 37% solution in water) in absolute ethanol (5 mL) was stirred at room temperature for 6 h. The product mixture was concentrated under vacuum, and the residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customthe residue was subjected to HPLC purification on C-18 stationary phase
  3. washeluted with water/acetonitrile/TFA mobile phase
  4. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-6e9e61f97ace4d87b6627e6354da0c5c
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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