Water → HCID 10193568, compound

HRID 1814900Notes

Reaction equation

HRID 1814900 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][NH:9][C:10]([C:12]2[C:13](=[O:24])[C:14]3[CH:21]=[C:20]([CH2:22]Cl)[O:19][C:15]=3[N:16]([CH3:18])[CH:17]=2)=[O:11])=[CH:6][CH:5]=1.C(=O)(O)[O-:28].[Na+].O>CN(C=O)C>[Cl:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][NH:9][C:10]([C:12]2[C:13](=[O:24])[C:14]3[CH:21]=[C:20]([CH2:22][OH:28])[O:19][C:15]=3[N:16]([CH3:18])[CH:17]=2)=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 10126210N-(4-Chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide

Product 1

HCID 10193568HCID 10193568, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2 N aq. sodium hydroxide (2.5 mL) was added to a solution of N-(4-chlorobenzyl)-2-(chloromethyl)-7-methyl-4-oxo-4,7-dihydrofuro[2,3-b]-pyridine-5-carboxamide (Example 2, 1.83 g) in DMF (40 mL). The mixture was heated and a sat. aq. sodium bicarbonate solution (10 mL) was added. The reaction mixture was allowed to cool to room temperature, was poured into water, and extracted with EtOAc (3×100 mL). The combined organic layers were concentrated. The crude product was purified by column chromatography (CH2Cl2/methanol, 100/1; 50/1; 20/1; 15/1) to afford 0.258 g of the title compound as a yellow solid. Physical characteristics. M.p. 229-230° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.63, 8.56, 7.42-7.32, 6.85, 5.53, 4.54, 4.51, 3.94; MS (EI) m/z 346 (M+).

Workup

  1. temperatureThe mixture was heated
  2. extractionextracted with EtOAc (3×100 mL)
  3. concentrationThe combined organic layers were concentrated
  4. customThe crude product was purified by column chromatography (CH2Cl2/methanol, 100/1; 50/1; 20/1; 15/1)

Sources & evidence

ORD record
ord-f3369fc4569647c98abf0ff283def672
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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