HCID 20038765, compound → HCID 20038771, compound

HRID 1904277Notes

Reaction equation

HRID 1904277 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[C:7]2[CH:13]=[N:14][NH:15][C:6]=12)[CH:2]=[CH2:3]>C(O)C.Cl.[Pd]>[NH2:12][CH2:11][C:10]1[C:5]([NH:4][CH2:1][CH2:2][CH3:3])=[C:6]2[NH:15][N:14]=[CH:13][C:7]2=[N:8][CH:9]=1

Participants

5

Reactant 1

HCID 20038765HCID 20038765, compound

Product 1

HCID 20038771HCID 20038771, compoundYield 37.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

A solution of 7-allylamino-6-cyano-1H-pyrazolo[4,3-b]pyridine (E2, 487 mg, 2.4 mmol) in ethanol (100 ml) and ethanolic hydrogen chloride (2 ml) was hydrogenated over 10% palladium on charcoal (200 mg) at 40° C. and atmospheric pressure for 48 h. The catalyst was filtered off and the solution was evaporated in vacuo. The resulting solid was dissolved in water (15 ml) and the solution was adjusted to pH 8 with 10% sodium carbonate solution. After washing with ethyl acetate, the aqueous solution was cooled at 4° C. for 2 days. A white solid separated and was filtered off and dried to give the title compound (185 mg, 37%), m.p. 97°-100° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solution was evaporated in vacuo
  3. dissolutionThe resulting solid was dissolved in water (15 ml)
  4. washAfter washing with ethyl acetate
  5. customA white solid separated
  6. filtrationwas filtered off
  7. customdried

Sources & evidence

ORD record
ord-d45f0c55da724c7cb4f4d381bf3c3d85
Source dataset
uspto-grants-1989_06
Patent number
US04837238

Reaction notes

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