Butyryl chloride → HCID 10421683, compound

HRID 497590Notes

Reaction equation

HRID 497590 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([NH2:17])=[N:13][NH:14]2)=[CH:10][CH:9]=1>N1C=CC=CC=1>[Cl:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([NH:17][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[N:13][NH:14]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 856286-chloro-1H-indazol-3-amine

Product 1

HCID 10421683HCID 10421683, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3 °C

Procedure

0.47 cm3 of butyryl chloride is added to 750 mg of 6-chloro-1H-indazole-3-amine in 10 cm3 of pyridine, after the reaction medium has been cooled to about 3° C. The medium is then allowed to return to 19° C. over 14 hours. The reaction medium is evaporated to dryness under reduced pressure (2 kPa; 40° C.). The residue is taken up in 50 cm3 of ethyl acetate, 50 cm3 of tetrahydrofuran and 50 cm3 of distilled water. The organic phase is washed again with 50 cm3 of distilled water and with 50 cm3 of saturated aqueous sodium chloride solution, and then dried over magnesium sulphate, filtered through a sinter funnel and evaporated under reduced pressure. The residue obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with cyclohexane/ethyl acetate (70/30 by volume) and collecting 25 cm3 fractions. The fractions containing the expected product are combined and then evaporated under reduced pressure (2 kPa; 40° C.). After drying (90 Pa; 45° C.), 200 mg of N-(6-chloro-1H-indazol-3-yl)-butanamide are obtained in the form of a white solid melting at 230° C.

Workup

  1. customThe reaction medium is evaporated to dryness under reduced pressure (2 kPa; 40° C.)
  2. washThe organic phase is washed again with 50 cm3 of distilled water and with 50 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered through a sinter funnel
  5. customevaporated under reduced pressure
  6. customThe residue obtained
  7. customis purified by chromatography under an argon pressure of 50 kPa
  8. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with cyclohexane/ethyl acetate (70/30 by volume)
  9. customcollecting 25 cm3 fractions
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 40° C.)
  12. dry with materialAfter drying (90 Pa; 45° C.), 200 mg of N-(6-chloro-1H-indazol-3-yl)-butanamide

Sources & evidence

ORD record
ord-666eea1756ec48f3b9b72c68914fda57
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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