Ethyl Acetate → HCID 86658571, compound

HRID 1520219Notes

Reaction equation

HRID 1520219 reaction equation
Cl[C:2]1[C:6]([C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8])=[CH:5][N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[N:3]=1.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.CCOC(C)=O>CN1C(=O)CCC1>[CH3:12][O:11][N:9]([CH3:10])[C:7]([C:6]1[C:2]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:3][N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:5]=1)=[O:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 86658572HCID 86658572, compound

Product 1

HCID 86658571HCID 86658571, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

According to Scheme 14 Step 1: A solution of 3-chloro-N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-pyrazole-4-carboxamide (0.97 mmol, 300 mg) and pyrrolidine (14.5 mmol, 1.03 g) in NMP (10 mL) was stirred at 220° C. for 40 minutes under microwave heating. AcOEt was then added and the organic phase was washed with water. The organic layer was dried over MgSO4, was filtered and was concentrated. The crude compound was purified by flash chromatography with silica gel using cyclohexane/AcOEt (100:0 to 50:50) to yield N-methoxy-1-(4-methoxybenzyl)-N-methyl-3-(pyrrolidin-1-yl)-1H-pyrazole-4-carboxamide (0.87 mmol, 300 mg, 90%) as an oil.

Workup

  1. temperatureheating
  2. washthe organic phase was washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationwas filtered
  5. concentrationwas concentrated
  6. customThe crude compound was purified by flash chromatography with silica gel

Sources & evidence

ORD record
ord-c4ca47bf63834f7884fbf09a82a2eb96
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

Loading…