Valeryl chloride → HCID 21248377, compound

HRID 620021Notes

Reaction equation

HRID 620021 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:20])[CH2:16][CH2:17][CH2:18][CH3:19]>>[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:20])[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

3

Reactant 2

HCID 61186Valeryl chlorideHCID 13747168HCID 13747168, compound

Product 1

HCID 21248377HCID 21248377, compoundYield 41%

Procedure

The title compound was prepared from 7-(2-hydroxyethylamino)-5-methyl-1H-pyrazolo[4,3-b]pyridine* (2.5 g) and valeryl chloride by the general method of Example 4. The product obtained was purified by column chromatography as described for Example 4 and then partitioned between ethyl acetate and water, the aqueous layer being brought to pH 9 with 10% sodium hydroxide. The ethyl acetate layer was separated and the aqueous layer extracted with ethyl acetate (×3). The combined organic layers were dried (anhydrous sodium sulphate) and evaporated to dryness to give a pale yellow gum which on trituration with ether and washing the resulting solid with ethyl acetate/ether gave the title compound as a pale yellow solid (1.48 g, 41%), m.p. 117°-119°.

Workup

  1. customThe product obtained
  2. customwas purified by column chromatography
  3. custompartitioned between ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. extractionthe aqueous layer extracted with ethyl acetate (×3)
  6. dry with materialThe combined organic layers were dried (anhydrous sodium sulphate)
  7. customevaporated to dryness
  8. customto give a pale yellow gum which on trituration with ether
  9. washwashing the resulting solid with ethyl acetate/ether

Sources & evidence

ORD record
ord-499ead0e9da048b0a662d72f4c6f24d6
Source dataset
uspto-grants-1989_04
Patent number
US04818754

Reaction notes

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