Sodium Methoxide → HCID 53241008, compound

HRID 1505429Notes

Reaction equation

HRID 1505429 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[N:15]=[CH:14][C:13]([NH:16][C:17]([NH:19][C:20]([CH3:26])([C:22](OC)=[O:23])[CH3:21])=[O:18])=[CH:12][CH:11]=2)=[C:5]([C:27]([F:30])([F:29])[F:28])[CH:4]=1)#[N:2].C[O-].[Na+]>CO>[CH3:21][C:20]1([CH3:26])[C:22](=[O:23])[N:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[C:27]([F:28])([F:29])[F:30])=[N:15][CH:14]=2)[C:17](=[O:18])[NH:19]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68322434HCID 68322434, compound2×

Product 1

HCID 53241008HCID 53241008, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl N-{[(6-{[4-cyano-2-(trifluoromethyl)phenyl]oxy}-3-pyridinyl)amino]carbonyl}-2-methylalaninate (Intermediate 165, 49 mg) in MeOH (10 mL) was heated at reflux for 10 min. Sodium methoxide (4 mg) was added to the hot reaction mixture and it was left refluxing for 2.5 hours. The solvent was evaporated to dryness and the residue obtained was purified by flash-chromatography (companion system, 12 g Si cartridge), with Cyclohexane/EtOAc as eluents from 70/30 to 50/50, to give two batches. The second batch was purified again by mass directed purification (METHOD K), leading to the desired compound which was gathered to the first batch, to afford the title compound as a white solid (8.2 mg).

Workup

  1. temperatureat reflux for 10 min
  2. waitwas left
  3. temperaturerefluxing for 2.5 hours
  4. customThe solvent was evaporated to dryness
  5. customthe residue obtained
  6. customwas purified by flash-chromatography (companion system, 12 g Si cartridge), with Cyclohexane/EtOAc as eluents from 70/30 to 50/50
  7. customto give two batches
  8. customThe second batch was purified again by mass
  9. custompurification (METHOD K)

Sources & evidence

ORD record
ord-f15651fb7d8d482bb1afc15f3ebd93f8
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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