Butyryl chloride → HCID 10060555, compound

HRID 497598

Reaction equation

HRID 497598 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[C:13]2[NH2:19])([O-:9])=[O:8]>N1C=CC=CC=1>[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][N:14]=[C:13]2[NH:19][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])([O-:9])=[O:8]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 31366553-Amino-5-nitroindazole

Product 1

HCID 10060555HCID 10060555, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

0.58 cm3 of butyryl chloride is added to 1 g of 5-nitro-1H-indazole-3-amine, prepared as described in, SU 742430 (CA: 94 :65676) in 25 cm3 of pyridine, and cooled to about 5° C. The reaction medium is allowed to return to about 19° C. over 12 hours. The insoluble material present is filtered off and the filtrate is then evaporated under reduced pressure (2 kPa; 50° C.). The residue is taken up in 15 cm3 of ethyl acetate and 15 cm3 of distilled water. 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 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume) and collecting 20 cm3 fractions. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). After drying (90 Pa; 50° C.), 480 mg of N-[5-nitro-1H-indazol-3-yl]butanamide are thus obtained in the form of a white solid.

Workup

  1. customprepared
  2. filtrationThe insoluble material present is filtered off
  3. customthe filtrate is then evaporated under reduced pressure (2 kPa; 50° C.)
  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 3.5 cm), eluting with a cyclohexane/ethyl acetate mixture (70/30 by volume)
  9. customcollecting 20 cm3 fractions
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. dry with materialAfter drying (90 Pa; 50° C.), 480 mg of N-[5-nitro-1H-indazol-3-yl]butanamide
  13. customare thus obtained in the form of a white solid

Sources & evidence

ORD record
ord-5115b65fb05c44499844b773fa32c8e9
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Linked notes

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