2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide → Azd-8330

HRID 2068927Notes

Reaction equation

HRID 2068927 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:27])[C:12](=[O:26])[C:13]([CH3:25])=[CH:14][C:15]=1[C:16]([NH:18][O:19][CH2:20][CH2:21][O:22]C=C)=[O:17]>CO>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:27])[C:12](=[O:26])[C:13]([CH3:25])=[CH:14][C:15]=1[C:16]([NH:18][O:19][CH2:20][CH2:21][OH:22])=[O:17]

Participants

3

Reactant 1

HCID 574691682-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-N-(2-(vinyloxy)ethoxy)-1,6-dihydropyridine-3-carboxamide

Product 1

HCID 16666708Azd-8330

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
0 °C

Procedure

The final product from Example 16 (25 mg) was placed in a Syn 10 (Radleys) reaction tube together with a magnetic stirrer, and the material was dissolved in methanol by the addition of one aliquot (1 mL) of methanol preheated to 50° C. with stirring. A further 5 mg of methanol was added to the reaction tube to ensure a super-saturated solution was produced on cooling. When the majority of the solid had dissolved, the resultant solution was filtered through a Pall 0.45 μm PTFE Acrodisc CR13 filter into a second tube at 50° C. in the Syn 10. The tube was then cooled to 0° C. at a rate of 3° C./min and held at 0° C. until the material had crystallized. The samples were filtered off, dried by suction then by standing in ambient conditions. The solids were carefully removed from the filter paper and examined by XRPD.

Workup

  1. custompreheated to 50° C.
  2. customwas produced
  3. temperatureon cooling
  4. dissolutionWhen the majority of the solid had dissolved
  5. filtrationthe resultant solution was filtered through a Pall 0.45 μm PTFE Acrodisc CR13
  6. filtrationfilter into a second tube at 50° C. in the Syn 10
  7. customheld at 0° C. until the material
  8. customhad crystallized
  9. filtrationThe samples were filtered off
  10. customdried by suction
  11. customThe solids were carefully removed from the filter paper

Sources & evidence

ORD record
ord-7cdaf48c71694fc1b91540b25d71daa7
Source dataset
uspto-grants-2012_10
Patent number
US08299076B2

Reaction notes

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