Phosphoric Acid → HCID 18386604, compound

HRID 2298432Notes

Reaction equation

HRID 2298432 reaction equation
COC(=O)[CH:4]([CH2:9][C:10]1[C:11]([NH:23][C:24]2[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=2[CH3:32])=[N:12][C:13]([CH3:22])=[CH:14][C:15]=1[NH:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:5](OC)=[O:6].P(=O)(O)(O)O>O.[OH-].[Na+]>[CH2:18]([CH:17]([N:16]1[C:15]2[C:10](=[C:11]([NH:23][C:24]3[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=3[CH3:32])[N:12]=[C:13]([CH3:22])[CH:14]=2)[CH2:9][CH2:4][C:5]1=[O:6])[CH2:20][CH3:21])[CH3:19]

Participants

5

Reactant 2

HCID 1004Phosphoric AcidHCID 53820580HCID 53820580, compound

Product 1

HCID 18386604HCID 18386604, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-pyridin-3-ylmethyl]-malonic acid dimethyl ester (100 mg, 0.219 mmol), 85% phosphoric acid (3 ml) and water (3 ml) was heated at reflux for 2 hours. The reaction mixture was cooled to rt, diluted with water and neutralized to pH 6 with dilute NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to dryness to give 61 mg of a yellow foam. The oil was purified through silca gel column chromatography using 10% EtOAc in hexane as eluent to give 41 mg of the title compound as a tan solid, mp 44-46° C. 1H NMR (CDC13) δ 6.87(s,2H), 6.36(s,1H), 5.64(brs,1H), 4.21(m,1H), 2.51(m,2H), 2.37(m,2H), 2.29(s,3H), 2.27(s,3H), 2.11(s,6H), 2.02(m,2H), 1.76(m,2H), 0.86(t,6H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a35a2b8192c8464b86a046fa2c2b23a4
Source dataset
uspto-grants-2002_12
Patent number
US06492520B1

Reaction notes

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