Potassium Carbonate → HCID 59565342, compound

HRID 1962856Notes

Reaction equation

HRID 1962856 reaction equation
[C:1]([C:3]([NH:7][C:8](=[O:30])[CH:9]([S:28][CH3:29])[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([CH3:21])[CH:20]=1)[N:17]=[CH:16][C:15]([C:22]#[C:23][Si](C)(C)C)=[CH:14]2)([CH3:6])[CH2:4][F:5])#[N:2].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CO>[C:1]([C:3]([NH:7][C:8](=[O:30])[CH:9]([O:10][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([CH3:21])[CH:20]=1)[N:17]=[CH:16][C:15]([C:22]#[CH:23])=[CH:14]2)[S:28][CH3:29])([CH3:6])[CH2:4][F:5])#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 59565363HCID 59565363, compound

Product 1

HCID 59565342HCID 59565342, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(1-cyano-2-fluoro-1-methyl-ethyl)-2-methylsulfanyl-2-(8-methyl-3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetamide (685 mg) in methanol (20 mL) was added potassium carbonate (107 mg). The reaction mixture was stirred at room temperature for 15 minutes. The mixture was poured on a saturated solution of sodium hydrogencarbonate and extracted with ethyl acetate (thrice), dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude was purified by chromatography eluting with cyclohexane/ethyl acetate (7:3 by volume), to give N-(1-cyano-2-fluoro-1-methyl-ethyl)-2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (476 mg) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (thrice)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by chromatography
  6. washeluting with cyclohexane/ethyl acetate (7:3 by volume)

Sources & evidence

ORD record
ord-3f4d909271e54c3bb04b2f80b1417c58
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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