3-Amino-1-propanol → 7-[3-hydroxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 651964Notes

Reaction equation

HRID 651964 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12.[NH2:12][CH2:13][CH2:14][CH2:15][OH:16]>C1(C)C(C)=CC=CC=1>[OH:16][CH2:15][CH2:14][CH2:13][NH:12][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[CH:9]=[N:10][NH:11][C:3]=12

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 116798717-Chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 137471677-[3-hydroxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridineYield 64.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7-Chloro-5-methyl-H-pyrazolo[4,3-b]pyridine (D4) (0.5 g, 0.003 mole) and 3-aminopropanol (0.75 g, 0.01 mole) in dry xylene (5 ml) were heated under reflux for 4 h. The solvent was removed under reduced pressure and the resulting oil recrystallised from methanol/ethyl acetate to give the hydrochloride salt of the title compound as a white crystalline solid (398 mg, 55%), m.p. 194°-196° C.

Workup

  1. temperatureunder reflux for 4 h
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting oil recrystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-d7c978636e4e422d9ec9779c34b9c386
Source dataset
uspto-grants-1987_06
Patent number
US04670432

Reaction notes

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