Sodium hydride → N-[3-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-yl]-N-propyl-propionamide

HRID 1671302Notes

Reaction equation

HRID 1671302 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([NH:19][C:20](=[O:23])[CH2:21][CH3:22])=[C:11]2[O:12][C:13]=1[CH3:14].[H-].[Na+].I[CH2:27][CH2:28][CH3:29]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([N:19]([CH2:27][CH2:28][CH3:29])[C:20](=[O:23])[CH2:21][CH3:22])=[C:11]2[O:12][C:13]=1[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 44815707N-(3-(2,4-Dichlorophenyl)-2,6-dimethylpyrazolo[5,1-b]oxazol-7-yl) propionamide

Product 1

HCID 44815706N-[3-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-yl]-N-propyl-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-(2,4-Dichlorophenyl)-2,6-dimethylpyrazolo[5,1-b]oxazol-7-yl) propionamide (634 mg, 1.800 mmol) is suspended in dry DMF (20 ml) and treated with NaH (60% in oil) (86 mg, 2.160 mmol) under N2 at RT. The mixture is stirred at RT for 10 minutes before cooling to 0° C. in an ice bath. 1-Iodopropane (0.263 ml, 2.70 mmol) is added dropwise and the reaction mixture is stirred at 0° C. for 1 hr. The solvent is removed in vacuo and the resulting residue is dissolved in EtOAc and washed with 1M NaOH, 1M HCl, H2O, brine, dried (MgSO4) and evaporated down to give a brown oil. Purification by chromatography on silica eluting with 0% to 50% EtOAc/iso-hexane affords the title compound as a clear oil; MS: m/z 394.1 [M+H]+

Workup

  1. temperaturebefore cooling to 0° C. in an ice bath
  2. stirringthe reaction mixture is stirred at 0° C. for 1 hr
  3. customThe solvent is removed in vacuo
  4. dissolutionthe resulting residue is dissolved in EtOAc
  5. washwashed with 1M NaOH, 1M HCl, H2O, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated down
  8. customto give a brown oil
  9. customPurification by chromatography on silica eluting with 0% to 50% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-56c8a66fd63549eb9f1c034969d92834
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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