Potassium Carbonate → HCID 86679897, compound

HRID 403465

Reaction equation

HRID 403465 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20](S(C)(=O)=O)[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:41][C:42]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][C:43]=1[OH:49].S([O-])(O)(=O)=O.[Na+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:34])[CH2:7][O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]2[O:17][C:18]3[N:19]=[C:20]([O:49][C:43]4[CH:44]=[C:45]([F:48])[CH:46]=[CH:47][C:42]=4[F:41])[N:21]=[C:22]([O:25][CH2:26][CH2:27][CH3:28])[C:23]=3[N:24]=2)=[CH:11][C:10]=1[CH3:33])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 949522,5-DifluorophenolHCID 516919Sodium BisulfateHCID 86679896Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

Product 1

HCID 86679897HCID 86679897, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 1.5 ml of N,N-dimethylformamide were added 62 mg of potassium carbonate and 32 mg of 2,5-difluoro-phenol. The mixture was stirred at room temperature for 12 h. Then the mixture was poured onto water, neutralized by addition of a 10% aqueous solution of sodium hydrogensulfate, and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. After filtration the solvent was distilled off in vacuo and the residue purified by preparative HPLC to yield 69 mg of the title compound.

Workup

  1. additionThen the mixture was poured onto water
  2. extractionextracted twice with ethyl acetate
  3. customThe combined organic layers were dried
  4. concentrationconcentrated in vacuo
  5. filtrationAfter filtration the solvent
  6. distillationwas distilled off in vacuo
  7. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-586565833103405e8359d34c96995918
Source dataset
uspto-grants-2014_06
Patent number
US08748436B2

Linked notes

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