HCID 21912453, compound → HCID 10224206, compound

HRID 2298429Notes

Reaction equation

HRID 2298429 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH:4]([CH2:9][C:10]1[C:11]([O: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]([O:7]C)=O>C(O)(=O)C>[CH3:1][O:2][C:3]([CH:4]1[CH2:9][C:10]2[C:15](=[CH:14][C:13]([CH3:22])=[N:12][C:11]=2[O:23][C:24]2[C:25]([CH3:32])=[CH:26][C:27]([CH3:31])=[CH:28][C:29]=2[CH3:30])[N:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:5]1=[O:7])=[O:33]

Participants

3

Reactant 1

HCID 21912453HCID 21912453, compound

Product 1

HCID 10224206HCID 10224206, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-ylmethyl]-malonic acid dimethyl ester (22 mg, 0.048 mmol) and 2 ml of acetic acid and bubbled through HCl (g) was heated at 130° C. for 30 hours. The reaction was cooled and concentrated to dryness. The residue was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 7 mg of the title compound. 1H NMR (CDCl3) δ 6.89(s,2H), 6.59(s,1H), 4.4(m,1H), 3.72(s,3H), 3.6-3.8(m,1H), 3.4-3.6(m,1H), 3.1-3.2(dd,1 H), 2.31(s,3H), 2.28(s,3H), 2.06(s,6H), 1.8-2.2(m,4H), 0.92(t,6H) ppm.

Workup

  1. custombubbled through HCl (g)
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated to dryness
  4. customThe residue was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ba238a0133eb49e4871688e8946f417a
Source dataset
uspto-grants-2002_12
Patent number
US06492520B1

Reaction notes

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