Ethyl Acetate → HCID 10268241, compound

HRID 585113Notes

Reaction equation

HRID 585113 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH2:12][NH2:13])[NH:10][N:11]=1.[C:20]([O:23][CH2:24][CH3:25])(=[O:22])C>C([O-])(O)=O.[Na+].ClC(OC)=O>[CH2:24]([O:23][C:20](=[O:22])[NH:13][CH2:12][C:9]1[NH:10][N:11]=[C:7]([C:6]2[O:5][C:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:3][C:2]=2[CH3:1])[CH:8]=1)[CH3:25]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 9899783HCID 9899783, compound

Product 1

HCID 10268241HCID 10268241, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6586Methyl chloroformateCatalystHCID 516892Sodium BicarbonateSolvent

Procedure

A heterogeneous mixture of the above-prepared C-[5-(4-Methyl-2-phenyl-oxazol-5-yl)-2H-pyrazol-3-yl]-methylamine (31 mg, 0.122 mmole, 1.0 eq) in ethyl acetate (0.5 ml) and 1.0N NaHCO3 (0.5 ml) was treated with excess methyl chloroformate (5 drops) and the mixture stirred at room temperature for 30 minutes. The mixture was partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with water and brine, then dried over anhydrous sodium sulfate and evaporated in vacuo to give a yellow solid. Silica gel chromatography eluting with (4:1) hexanes-acetone provided 28 mg (74%) of the title compound as a white solid. 1H NMR (DMSO-d6): δ 2.6 (s, 3H), 3.6 (s, 3H), 4.25 (m, 2H), 6.5 (s, 1H), 7.5 (m, 3H), 7.7 (bm, 1H), 8.0 (m, 2H).

Workup

  1. customThe mixture was partitioned between ethyl acetate and saturated NaHCO3
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customto give a yellow solid
  6. washSilica gel chromatography eluting with (4:1) hexanes-acetone

Sources & evidence

ORD record
ord-f759b92268bf4d84b64c56d3756069b2
Source dataset
uspto-grants-2005_08
Patent number
US06930116B2

Reaction notes

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