Methane → HCID 13824264, compound

HRID 1906854Notes

Reaction equation

HRID 1906854 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][N:12]2[C:17]([C:18]3[CH:19]=[C:20]([N:24]([CH3:29])[C:25](=[O:28])[CH2:26]Br)[CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:15]=[N:14][C:13]=12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][NH:31][CH3:32].C.CCCCCC>C(O)C>[C:1]([C:9]1[CH:10]=[N:11][N:12]2[C:17]([C:18]3[CH:19]=[C:20]([N:24]([CH3:29])[C:25](=[O:28])[CH2:26][N:31]([CH3:32])[CH3:30])[CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:15]=[N:14][C:13]=12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 674DimethylamineHCID 8058HexaneHCID 13824263HCID 13824263, compound

Product 1

HCID 13824264HCID 13824264, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

A suspension of 1.7 g of N-[3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-2-bromo-N-methylacetamide in 100 ml of ethanol was treated with gaseous dimethylamine until a solution resulted. This was then placed in a pressure bottle and kept at room temperature for 16 hours. The ethanol was removed in vacuo and the residue partitioned between 50 ml of saturated aqueous sodium bicarbonate solution and 100 ml of methylene chloride. The methylene chloride layer was separated, dried over magnesium sulfate, and the methylene chloride removed in vacuo. The residue was dissolved in 50 ml of methylene chloride, the solution then treated with hexane at the boiling point until turbidity was present. Cooling at -10° C. gave a low yield of tacky solid. The cold mixture was treated with activated charcoal, clarified and the filtrate again treated at the boiling point with hexane until turbidity occurred. Cooling at -10° C. gave 0.3 g of the desired compound as a bright yellow solid, mp 166°-168° C.

Workup

  1. customresulted
  2. customThe ethanol was removed in vacuo
  3. customthe residue partitioned between 50 ml of saturated aqueous sodium bicarbonate solution and 100 ml of methylene chloride
  4. customThe methylene chloride layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customthe methylene chloride removed in vacuo
  7. dissolutionThe residue was dissolved in 50 ml of methylene chloride
  8. additionthe solution then treated with hexane at the boiling point until turbidity
  9. customgave a low yield of tacky solid
  10. temperatureCooling at -10° C.

Sources & evidence

ORD record
ord-efa5d23837a94c8b98454ec8ea582aaf
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

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