Heptane → HCID 90023954, compound

HRID 1484526Notes

Reaction equation

HRID 1484526 reaction equation
C[O:2][C:3]([NH:5][N:6]=[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([O:24][C:25]([F:28])([F:27])[F:26])[CH:18]=2)=[CH:14][CH:15]=1)[CH3:8])=O.C(=O)([O-])[O-].[K+].[K+].CCCCCCC>C(#N)C.O.C(OCC)(=O)C.CC(OC)(C)C>[CH3:8][C:7]1[N:9]([C:10]2[CH:11]=[N:12][C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([O:24][C:25]([F:27])([F:28])[F:26])[CH:18]=3)=[CH:14][CH:15]=2)[C:3](=[O:2])[NH:5][N:6]=1

Participants

8

Reactant 3

HCID 8900HeptaneHCID 11430Potassium CarbonateHCID 178502532HCID 178502532, compound2×

Product 1

HCID 90023954HCID 90023954, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of methyl-2-[1-({6-[4-methyl-3-(trifluoromethoxy)phenoxy]pyridin-3-yl}amino)ethylidene]hydrazinecarboxylate (Intermediate 33, 360 mg, 0.90 mmol) in 3 mL of acetonitrile and some drops of water, potassium carbonate (187 mg) was added. The resulting solution was stirred at room temperature for 24 hrs until complete conversion. The mixture was diluted with water (5 mL) and ethyl acetate (5 mL) and phases were separated. The aqueous phase was back-extracted with ethyl acetate (2×20 mL). The combined organics were dried over Na2SO4, filtered and concentrated to give 280 mg as pale orange foam. This material was dissolved in MTBE (1 mL) and n-heptane was added until a solid precipitated. This was collected by filtration to give 234 mg of the title compound as white solid.

Workup

  1. customwere separated
  2. extractionThe aqueous phase was back-extracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give 280 mg as pale orange foam
  7. customprecipitated
  8. filtrationThis was collected by filtration

Sources & evidence

ORD record
ord-b10f0718cab347f282c12c91c3cd37fc
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

Loading…