p-Toluenesulfonic acid → HCID 9908466, compound

HRID 1166178Notes

Reaction equation

HRID 1166178 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](Cl)[C:5]2[C:6](=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[N:9]([CH3:11])[N:10]=2)[N:7]=1.[C:21]1([CH3:31])[CH:26]=CC(S(O)(=O)=O)=CC=1>C(NCCC)CC>[CH3:1][C:2]1[CH:3]=[C:4]([N:7]([CH2:26][CH2:21][CH3:31])[CH2:2][CH2:3][CH3:4])[C:5]2[C:6](=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=3[Cl:19])[N:9]([CH3:11])[N:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22997479HCID 22997479, compound

Product 1

HCID 9908466HCID 9908466, compound

Reagents, catalysts & solvents 1

HCID 8902DipropylamineSolvent

Procedure

Intermediate (5) was suspended in dipropylamine (1 ml) and p-toluenesulfonic acid (30 mg) and heated to 200° C. for 2 hours in a sealed tube. The reaction mixture was cooled and partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated, dried and concentrated. The residue was purified over silica gel (eluens: ethyl acetate/hexanes), yielding 5-methyl-7-(dipropylamino)-2-methyl-3-(2,4-dichlorophenyl)pyrazolo[4,3-b]pyridine (compound 1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel (eluens: ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e039d64d128a4972877b4fc85d60b773
Source dataset
uspto-grants-2003_09
Patent number
US06613777B1

Reaction notes

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