6-Acetyl-7-chloro-1H-pyrazolo[4,3-b]pyridine → 6-Acetyl-7-allylamino-1H-pyrazolo[4,3-b]pyridine

HRID 1904278Notes

Reaction equation

HRID 1904278 reaction equation
[C:1]([C:4]1[C:5](Cl)=[C:6]2[NH:12][N:11]=[CH:10][C:7]2=[N:8][CH:9]=1)(=[O:3])[CH3:2]>C(N)C=C>[C:1]([C:4]1[C:5]([NH:8][CH2:7][CH:6]=[CH2:5])=[C:6]2[NH:12][N:11]=[CH:10][C:7]2=[N:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 200387626-Acetyl-7-chloro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 200387686-Acetyl-7-allylamino-1H-pyrazolo[4,3-b]pyridineYield 152.3%

Reagents, catalysts & solvents 1

HCID 7853AllylamineSolvent

Procedure

A solution of 6-acetyl-7-chloro-1H-pyrazolo[4,3-b]pyridine (D15, 340 mg, 1.7 mmol) in allylamine (5 ml) was stirred at room temperature for 16 h. Excess allylamine was removed in vacuo and the residue was dissolved in aqueous methanol. The solution was adjusted to pH 8 with 10% sodium carbonate solution, and extracted with ethyl acetate (4×50 ml). The extracts were washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo to give a sticky solid. This was crystallised from ethyl acetate/ethanol to give the title compound (280 mg, 75%), m.p. 211°-213° C. Found: C, 60.49; H, 5.81; N, 25.55. C11H12N4O requires C, 61.10; H, 5.59; N, 25.91%.

Workup

  1. customExcess allylamine was removed in vacuo
  2. dissolutionthe residue was dissolved in aqueous methanol
  3. extractionextracted with ethyl acetate (4×50 ml)
  4. washThe extracts were washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto give a sticky solid
  8. customThis was crystallised from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-b95657d9ac474680bd25249c27055511
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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