Methanol → HCID 21248374, compound

HRID 620020Notes

Reaction equation

HRID 620020 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]2[CH:12]=[N:13][NH:14][C:6]=12.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO>O>[C:15]([O:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]2[CH:12]=[N:13][NH:14][C:6]=12)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7412Benzoyl chlorideHCID 13747168HCID 13747168, compound

Product 1

HCID 21248374HCID 21248374, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from 7-(2-hydroxyethyl-amino)-5-methyl-1H-pyrazolo[4,3-b]pyridine (2 g) and benzoyl chloride by the general method of Example 4 without the addition of methanol. The crude reaction mixture was poured into a large excess of water and extracted with ethyl acetate (×3). The combined organic layers were washed with water (×2), dried with anhydrous sodium sulphate, filtered and evaporated to dryness. The resulting intermediate dibenzoylated compound was recrystallized from carbon tetrachloride/60°-80° C. petrol to give a pale yellow solid, m.p. 136°-138° C.

Workup

  1. customThe crude reaction mixture
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layers were washed with water (×2)
  4. dry with materialdried with anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customwas recrystallized from carbon tetrachloride/60°-80° C. petrol
  8. customto give a pale yellow solid, m.p. 136°-138° C.

Sources & evidence

ORD record
ord-145283af0e7d4ce29dd99739618a62d3
Source dataset
uspto-grants-1989_04
Patent number
US04818754

Reaction notes

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