Dimethylformamide → HCID 71089566, compound

HRID 331030Notes

Reaction equation

HRID 331030 reaction equation
[N:1]1([C:6]2[N:11]=[N:10][CH:9]=[C:8](O)[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Br)(Br)([Br:15])=O.CN(C=O)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[Br:15][C:8]1[CH:7]=[C:6]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[N:11]=[N:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24613Phosphorus oxybromideHCID 178516811HCID 178516811, compound

Product 1

HCID 71089566HCID 71089566, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

6-(1-pyrrolidinyl)-4-pyridazinol (D47) (35 mg, 0.212 mmol) was suspended in toluene (2 mL), followed by addition of phosphorus oxybromide (121 mg, 0.424 mmol). The reaction mixture was heated to 110° C. for 2 hours. The reaction was cooled to RT followed by addition of DMF (2.0 mL). The reaction was then heated at 110° C. again for 2 hours. Reaction mixture was allowed to cool to RT, and then poured onto crush ice portionwise with stirring. The mixture was neutralized with 5M NaOH and then extracted with ethyl acetate (3×20 mL). The combined organics were dried and concentrated down to give the title compound (40 mg) which was taken on to the next step without purification. LCMS (A): m/z (M+H)+ 228/230, C8H10BrN3 requires 227/229 (acidic).

Workup

  1. temperatureThe reaction was cooled to RT
  2. temperatureThe reaction was then heated at 110° C. again for 2 hours
  3. customReaction mixture
  4. temperatureto cool to RT
  5. additionpoured
  6. customonto crush ice portionwise
  7. extractionextracted with ethyl acetate (3×20 mL)
  8. customThe combined organics were dried
  9. concentrationconcentrated down

Sources & evidence

ORD record
ord-49c7f304f003409680e9d7d5019a1ad9
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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