Vanillin → 5-(4-Formyl-2-methoxyphenoxy)pyrazine-2-carboxamide

HRID 131015Notes

Reaction equation

HRID 131015 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.[O:11]=[CH:12][C:13]1[CH:21]=[CH:20][C:18]([OH:19])=[C:15]([O:16][CH3:17])[CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:12]([C:13]1[CH:21]=[CH:20][C:18]([O:19][C:2]2[N:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=2)=[C:15]([O:16][CH3:17])[CH:14]=1)=[O:11]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 1814505-Chloropyrazinamide

Product 1

HCID 597299775-(4-Formyl-2-methoxyphenoxy)pyrazine-2-carboxamideYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 5-chloropyrazine-2-carboxamide (Example 387, Part A) (0.374 g, 2.34 mmol) and vanillin (0.361 g, 2.34 mmol) in DMF (23.7 mL). Add K2CO3 (0.821 g, 8.94 mmol) and heat at 100° C. for 1.5 hours. Concentrate the reaction mixture. Take the solid up in water (50 mL) and extract with dichloromethane (3×100 mL). Dry the organic layer over Na2SO4, filter and concentrate to give the title compound (0.625 g, 96.4%): TOF MS ES+ 274.1 (M+H)+, HRMS calcd for C13H12N3O4 274.0828 (M+H)+, found 274.0829, time 0.55 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95 over 19 min], tR=10.2 min, 98.1% purity.

Workup

  1. concentrationConcentrate the reaction mixture
  2. extractionextract with dichloromethane (3×100 mL)
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-638bcc367f0146ce8d179251bc8644cb
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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