Potassium Carbonate → 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

HRID 1962863Notes

Reaction equation

HRID 1962863 reaction equation
[OH:1][CH2:2][C:3]([NH:8][C:9](=[O:31])[CH:10]([S:29][CH3:30])[O:11][C:12]1[CH:13]=[C:14]2[C:19](=[C:20]([CH3:22])[CH:21]=1)[N:18]=[CH:17][C:16]([C:23]#[C:24][Si](C)(C)C)=[CH:15]2)([CH2:5][O:6][CH3:7])[CH3:4].C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[C:23]([C:16]1[CH:17]=[N:18][C:19]2[C:14]([CH:15]=1)=[CH:13][C:12]([O:11][CH:10]([S:29][CH3:30])[C:9]([NH:8][C:3]([CH2:5][O:6][CH3:7])([CH3:4])[CH2:2][OH:1])=[O:31])=[CH:21][C:20]=2[CH3:22])#[CH:24]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 68422187HCID 68422187, compound

Product 1

HCID 595653242-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamideYield 87.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-2-(8-methyl-3-trimethylsilanylethynyl-quinolin-6-yloxy)-acetamide (650 mg) in methanol (16 ml) was treated with potassium carbonate (97 mg) at room temperature. The reaction mixture was stirred for 1 h. The reaction mixture was diluted with ethyl acetate and washed with sat. aq. sodium hydrogen carbonate. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane 2:2:1) to give 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (480 mg) as a white solid as mixture of diastereoisomers.

Workup

  1. washwashed with sat. aq. sodium hydrogen carbonate
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane 2:2:1)

Sources & evidence

ORD record
ord-8079e661de884cfb9504423f495d275c
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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