Nitrogen → 2-(3-Acetyl-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester

HRID 1189389Notes

Reaction equation

HRID 1189389 reaction equation
N#N.[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13]OS(C)(=O)=O)[O:11][CH:12]=1)=[O:7])[CH3:4].Cl.[NH:20]1[C:24]([C:25](=[O:27])[CH3:26])=[CH:23][CH:22]=[N:21]1.C([O-])([O-])=O.[K+].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CC(C)=O>[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13][N:21]2[CH:22]=[CH:23][C:24]([C:25](=[O:27])[CH3:26])=[N:20]2)[O:11][CH:12]=1)=[O:7])[CH3:4]

Participants

7

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27996231-(1H-pyrazol-5-yl)ethan-1-one hydrochlorideHCID 866649112-Methanesulfonyloxymethyl-oxazole-4-carboxylic acid ethyl ester

Product 1

HCID 671284172-(3-Acetyl-pyrazol-1-ylmethyl)-oxazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-methanesulfonyloxymethyl-oxazole-4-carboxylic acid ethyl ester (160 mg, 0.64 mmol) and TBAB (41 mg, 0.13 mmol) in dry acetone (9.0 mL) was treated at rt with a solution of 1-(1H-pyrazol-5-yl)ethan-1-one hydrochloride (99 mg, 0.64 mmol) and K2CO3 (448 mg, 3.21 mmol) in acetone (4.0 mL). After stirring at rt for 2 days, the solvent was removed under reduced pressure. The residue was partitioned between water and EA, the two layers were separated and the aq. layer was extracted twice with EA. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:2 hept-EA)=0.33. LC-MS-conditions 02: tR=0.80 min, [M+H]+=263.97.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between water and EA
  3. customthe two layers were separated
  4. extractionthe aq. layer was extracted twice with EA
  5. dry with materialextracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customPurification of the residue by FC (2:1 hept-EA)

Sources & evidence

ORD record
ord-6e597c242ce849e78def9c50611593f7
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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