Potassium Carbonate → HCID 178492556, compound

HRID 710059Notes

Reaction equation

HRID 710059 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[O:6][CH2:7][C:8]#[N:9].[NH:15]([C:17]([C@@H:19]1[CH2:23][CH2:22][CH2:21][N:20]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=O)[NH2:16].C([O-])([O-])=O.[K+].[K+]>C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[O:6][CH2:7][C:8]1[NH:9][C:17]([C@@H:19]2[CH2:23][CH2:22][CH2:21][N:20]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:15][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10014050tert-Butyl (2S)-2-(hydrazinecarbonyl)pyrrolidine-1-carboxylateHCID 189913533,4-Dimethoxyphenoxyacetonitrile

Product 1

HCID 178492556HCID 178492556, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
160 °C

Procedure

To a n-butanol (10 ml) solution of 2-(3,4-dimethoxyphenoxy)acetonitrile (1.26 g) and (S)-t-butyl 2-(hydrazinecarbonyl)pyrrolidine-1-carboxylate (500 mg), K2CO3 (150 mg) was added. The resulting mixture was stirred at 160° C. for an hour under microwave irradiation. After distilling off the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography and NH-form silica gel chromatography to give the titled compound (281 mg).

Workup

  1. distillationAfter distilling off the solvent under reduced pressure, water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography and NH-form silica gel chromatography

Sources & evidence

ORD record
ord-0a0cbec2585c43d78f9151704aaf8d69
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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