Water → HCID 9999005, compound

HRID 1813918Notes

Reaction equation

HRID 1813918 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]=1NC(CC)CC)[C:5]([O:7]C)=O.P(=O)(O)(O)O.[OH2:39]>>[CH2:4]([CH:9]([O:39][C:15]1[CH:14]=[C:13]([CH3:22])[N:12]=[C:11]2[C:10]=1[CH2:9][CH2:4][C:5](=[O:7])[N:23]2[C:24]1[C:29]([CH3:30])=[CH:28][C:27]([CH3:31])=[CH:26][C:25]=1[CH3:32])[CH2:10][CH3:15])[CH3:5]

Participants

4

Reactant 3

HCID 962Water2×HCID 1004Phosphoric AcidHCID 53820580HCID 53820580, compound

Product 1

HCID 9999005HCID 9999005, compound

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 room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated to dryness to give 91 mg of a clear oil. The oil was purified through silca gel column chromatography using 10% methanol (MeOH) in methylene chloride (CHCl2) as eluent to give a tan crystals, mp 138-140° C. 1H NMR (CDCl3) δ 6.93(s,2H), 6.31(s,1H), 4.21(m,1H), 2.93(m,2H), 2.76(m,2H), 2.31(s,3H), 2.19(s,3H), 1.99(s,6H), 1.71(m,4H), 0.96(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-2032f4982090464e873e1632a3d659c5
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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