Acetyl chloride → HCID 10058938, compound

HRID 497589Notes

Reaction equation

HRID 497589 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([NH2:15])=[N:11][NH:12]2)=[CH:8][CH:7]=1>N1C=CC=CC=1>[Cl:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]([NH:15][C:1](=[O:3])[CH3:2])=[N:11][NH:12]2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 856286-chloro-1H-indazol-3-amine

Product 1

HCID 10058938HCID 10058938, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3 °C

Procedure

0.32 cm3 of predistilled acetyl 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 48 hours. The reaction medium is evaporated to dryness under reduced pressure (2 kPa; 40° C.). The residue is taken up in 75 cm3 of ethyl acetate and 50 cm3 of distilled water. The organic phase is washed again with 50 cm3 of distilled water 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 4 cm), eluting with a cyclohexane/ethyl acetate mixture (60/40 by volume) and collecting 35 cm3 fractions. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 40° C.). After drying (90 Pa; 45° C.), 700 mg of N-(6-chloro-1H-indazol-3-yl)-acetamide, melting at 240° C., are obtained.

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
  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 4 cm), eluting with a cyclohexane/ethyl acetate mixture (60/40 by volume)
  9. customcollecting 35 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.), 700 mg of N-(6-chloro-1H-indazol-3-yl)-acetamide, melting at 240° C.
  13. customare obtained

Sources & evidence

ORD record
ord-35031b17da634ffebc0eb292793295b1
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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