Epichlorohydrin → HCID 22498722, compound

HRID 1814886Notes

Reaction equation

HRID 1814886 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[CH:19]=[C:18]([CH2:20][NH:21][CH3:22])[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH2:26]([CH:28]1[O:30]C1)[Cl:27]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:23])[C:12]3[CH:19]=[C:18]([CH2:20][NH:21][CH2:22][CH:28]([OH:30])[CH2:26][Cl:27])[O:17][C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 10150223HCID 10150223, compound

Product 1

HCID 22498722HCID 22498722, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A sealed tube was charged with a mixture of N-(4-chlorobenzyl)-7-methyl-2-((methylamino)methyl)-4-oxo-4,7-dihydrofuro[2,3-b]pyridine-5-carboxamide (Example 62, 3.21 g), epi-chlorohydrin (0.90 mL), and ethanol (80 mL). The mixture was heated to 80° C. overnight and then concentrated. The crude product was purified by column chromatography (acetone/CHCl3/NH4OH, 1/1/0.5%) to yield 1.62 g of the title compound as a white solid. Physical characteristics. 1H NMR (400 MHz, DMSO-d6) δ 10.65, 8.55, 7.39, 7.33, 5.08, 4.54, 3.93, 3.84, 3.75-3.65, 3.56, 2.53, 2.39, 2.28.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by column chromatography (acetone/CHCl3/NH4OH, 1/1/0.5%)

Sources & evidence

ORD record
ord-0c647538dfd842388a209f67dba848e6
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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