Methanol → 7-[3-Pentanoyloxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

HRID 620018Notes

Reaction equation

HRID 620018 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[CH:13]=[N:14][NH:15][C:7]=12.[C:16](Cl)(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20].CO.CCOCC>N1C=CC=CC=1.O1CCOCC1>[C:16]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]2[CH:13]=[N:14][NH:15][C:7]=12)(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 61186Valeryl chlorideHCID 137471677-[3-hydroxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 212483807-[3-Pentanoyloxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent2×

Procedure

7-[3-Hydroxypropylamino]-5-methyl-1H-pyrazolo[4,3-b]-pyridine,* (0.15 g, 0.73 mmol) was suspended in dry pyridine (2 ml) and 1,4-dioxan (2 ml) and cooled in an ice-bath. A solution of valeryl chloride (0.18 ml, 2.1 equiv.) in dioxan (1.5 ml) was added dropwise with stirring and then left at room temperature overnight. Methanol (10 ml) was added and the resulting solution stirred for 1 h and then solvents removed under reduced pressure. The residue was chromatographed on basic alumina eluting initially with ethyl acetate rising to 30% methanol/ethyl acetate. After removal of solvent a colourless oil was obtained, which on trituration with ether gave the title compound as a white solid, m.p. 92°-95° C.

Workup

  1. stirringthe resulting solution stirred for 1 h
  2. customsolvents removed under reduced pressure
  3. customThe residue was chromatographed on basic alumina eluting initially with ethyl acetate rising to 30% methanol/ethyl acetate
  4. customAfter removal of solvent a colourless oil
  5. customwas obtained

Sources & evidence

ORD record
ord-f466e1e089224f1c8578aa145e4a2fac
Source dataset
uspto-grants-1989_04
Patent number
US04818754

Reaction notes

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