Dimethylformamide → HCID 16063558, compound

HRID 1993933Notes

Reaction equation

HRID 1993933 reaction equation
[C:1]12([C:11]3[C:12](=[O:17])[NH:13][NH:14][C:15]=3[CH3:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[CH2:19][CH2:20][CH2:21]Br.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.C(=O)(O)[O-].[Na+]>[C:1]12([C:11]3[C:12](=[O:17])[N:13]4[CH2:19][CH2:20][CH2:21][N:14]4[C:15]=3[CH3:16])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 13675783HCID 13675783, compound

Product 1

HCID 16063558HCID 16063558, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

Into a sealable pressure vessel was placed 4-adamantan-1-yl-5-methyl-1,2-dihydro-pyrazol-3-one (3.5 g) (as described in example 48) along with 1,3-dibromopropane (6.1 g) and DMF (40 mL) and one equivalent of solid potassium carbonate. The reaction vessel was sealed and the solution was heated to 100° C. for 20 hours. The reaction was then allowed to cool and diluted with EtOAc and saturated sodium bicarbonate solution. The phases were separated and the aqueous phase was extracted with further EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. The obtained residue was purified via ISCO Combiflash chromatography (over silica column, eluting with EtOAc/heptane) to afford 2-adamantan-1-yl-3-methyl-6,7-dihydro-5H-pyrazolo[1,2-a]pyrazol-1-one (0.821 g) as a white solid. MS (ESI+): 273.0 [M+H]+).

Workup

  1. customInto a sealable pressure vessel was placed
  2. customThe reaction vessel was sealed
  3. temperatureto cool
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with further EtOAc
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe obtained residue was purified via ISCO Combiflash chromatography (over silica column, eluting with EtOAc/heptane)

Sources & evidence

ORD record
ord-f336daa3ce454f5387cd0354dd1f9191
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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