Butyryl chloride → HCID 10444180, compound

HRID 497595Notes

Reaction equation

HRID 497595 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([NH2:17])=[N:11][NH:12]2>N1C=CC=CC=1>[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([NH:17][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[N:11][NH:12]2

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 3134443-Amino-4-chloroindazole

Product 1

HCID 10444180HCID 10444180, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

0.23 cm3 of butyryl chloride is added to 1 g of 4-chloro-1H-indazole-3-amine, prepared as described in patent EP 90 972, in 10 cm 3 of pyridine, cooled to about 10° C. The temperature is allowed to return to about 19° C. over 17 hours. The reaction medium is evaporated under reduced pressure (2 kPa; 50° C.). The residue is taken up in 25 cm3 of ethyl acetate and 25 cm3 of distilled water. The organic phase is washed with 2×25 cm3 of distilled water and with 25 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered through a sinter funnel and then evaporated under reduced pressure (2 kPa; 50° C.). The residue 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 dichloromethane/methanol mixture (99/1 by volume) and collecting 30 cm3 fractions. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). 80 mg of N-[4-chloro-1H-indazol-3-yl]butanamide are thus obtained in the form of a white solid melting at 198° C.

Workup

  1. customprepared
  2. customThe reaction medium is evaporated under reduced pressure (2 kPa; 50° C.)
  3. washThe organic phase is washed with 2×25 cm3 of distilled water and with 25 cm3 of saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. filtrationfiltered through a sinter funnel
  6. customevaporated under reduced pressure (2 kPa; 50° C.)
  7. customThe residue is 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 dichloromethane/methanol mixture (99/1 by volume)
  9. customcollecting 30 cm3 fractions
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)

Sources & evidence

ORD record
ord-5b1a27bbbb20491db496ff935b4cc250
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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