Potassium Carbonate → N-(1-ethyl-1H-pyrazol-5-yl)-2-(2-formyl-3-(methoxymethoxy)phenoxy)-N-isopropylacetamide

HRID 1770807Notes

Reaction equation

HRID 1770807 reaction equation
Cl[CH2:2][C:3]([N:5]([C:9]1[N:13]([CH2:14][CH3:15])[N:12]=[CH:11][CH:10]=1)[CH:6]([CH3:8])[CH3:7])=[O:4].[OH:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][O:27][CH3:28])[C:18]=1[CH:19]=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([N:13]1[C:9]([N:5]([CH:6]([CH3:8])[CH3:7])[C:3](=[O:4])[CH2:2][O:16][C:17]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][O:27][CH3:28])[C:18]=2[CH:19]=[O:20])=[CH:10][CH:11]=[N:12]1)[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15312034AR-260HCID 1180727952-chloro-N-(1-ethyl-1H-pyrazol-5-yl)-N-isopropylacetamide

Product 1

HCID 118072802N-(1-ethyl-1H-pyrazol-5-yl)-2-(2-formyl-3-(methoxymethoxy)phenoxy)-N-isopropylacetamideYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-N-(1-ethyl-1H-pyrazol-5-yl)-N-isopropylacetamide (0.39 g, 1.7 mmol) and 2-hydroxy-6-(methoxymethoxy)benzaldehyde (0.309 g, 1.7 mmol) were dissolved in DMF (8.5 ml) and purged with N2 gas. Potassium carbonate (0.47 g, 3.4 mmol) was added and the mixture was stirred in a heat block at 60° C. After 2 h, the reaction was cooled and partitioned into ethyl acetate (100 ml) and water (100 ml). The phases were separated and the aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phases were washed with water (50 ml) and a saturated aqueous sodium chloride solution (50 ml), and dried over sodium sulfate. After evaporation the residue was purified by silica gel chromatography (5-50% ethyl acetate/hexanes) to give 0.38 g (59%) of N-(1-ethyl-1H-pyrazol-5-yl)-2-(2-formyl-3-(methoxymethoxy)phenoxy)-N-isopropylacetamide as a faintly-colored viscous oil. MS (ESI) m/z 376 [M+H]+.

Workup

  1. custompurged with N2 gas
  2. temperaturethe reaction was cooled
  3. custompartitioned into ethyl acetate (100 ml) and water (100 ml)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (2×50 ml)
  6. washThe combined organic phases were washed with water (50 ml)
  7. dry with materiala saturated aqueous sodium chloride solution (50 ml), and dried over sodium sulfate
  8. customAfter evaporation the residue
  9. customwas purified by silica gel chromatography (5-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a19e3805b7f247f6bf37ea207df1fd09
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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