Sodium Formate → HCID 59846181, compound

HRID 1697081Notes

Reaction equation

HRID 1697081 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23]Br)=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([CH3:27])[N:8]=2)=[O:4].C([O-])=[O:35].[Na+]>CCO>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13](=[O:26])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:25])[CH2:23][OH:35])=[CH:18][CH:17]=1)=[CH:11][CH:10]=[C:9]([CH3:27])[N:8]=2)=[O:4]

Participants

4

Reactant 2

HCID 2723810Sodium FormateHCID 59846182HCID 59846182, compound

Product 1

HCID 59846181HCID 59846181, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-[4-(2-bromo-acetyl)-benzyl]-7-methyl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (38 mg, 0.075 mmol) and sodium formate (25.5 mg, 5 eq.) in EtOH (15 mL) was heated at 80° C. overnight. The reaction mixture was concentrated under reduced pressure and filtered. The crude residue was purified by preparative TLC (EtOAc/hexane, 60/40) to afford 14 mg of 3-[4-(2-hydroxy-acetyl)-benzyl]-7-methyl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester as an off-white powder. MS=443 [M+H]+; MP=189.9-192.9° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered
  3. customThe crude residue was purified by preparative TLC (EtOAc/hexane, 60/40)

Sources & evidence

ORD record
ord-4c61c7f6603c4d4b90d5a51135a71fe6
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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