Butyryl chloride → HCID 22319597, compound

HRID 497718Notes

Reaction equation

HRID 497718 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[Br:7][C:8]1[C:16]([F:17])=[C:15]2[C:11]([C:12]([NH2:18])=[N:13][NH:14]2)=[C:10]([F:19])[C:9]=1[F:20]>N1C=CC=CC=1>[Br:7][C:8]1[C:16]([F:17])=[C:15]2[C:11]([C:12]([NH:18][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[N:13][NH:14]2)=[C:10]([F:19])[C:9]=1[F:20]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 22319617HCID 22319617, compound

Product 1

HCID 22319597HCID 22319597, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3 °C

Procedure

0.82 cm3 of butyryl chloride is added to 2.1 g of 6-bromo-4,5,7-trifluoro-1H-indazole-3-amine, prepared previously, in 20 cm3 of pyridine, after cooling to about 3° C., and the mixture is then left at room temperature for 76 hours. The reaction medium is concentrated under reduced pressure (2 kPa; 40° C.) and the residue is taken up in 100 cm3 of ethyl acetate, 100 cm3 of tetrahydrofuran and 40 cm3 of water. The organic phase is washed with 2×40 cm3 of distilled water and then with 40 cm3 of saturated aqueous sodium chloride solution. After drying over magnesium sulphate, filtration and concentration under reduced pressure (2 kPa; 40° C.), 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 (80/20 by volume). The fractions containing the expected product are combined and then evaporated under reduced pressure (2 kPa; 40° C.); after drying (90 Pa; 40° C.), 0.53 g of N-(6-bromo-4,5,7-trifluoro-1H-indazol-3-yl)butanamide is obtained in the form of a pink solid melting at 255°-257° C.

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure (2 kPa; 40° C.)
  2. washThe organic phase is washed with 2×40 cm3 of distilled water
  3. dry with materialAfter drying over magnesium sulphate, filtration and concentration under reduced pressure (2 kPa; 40° C.)
  4. customthe residue obtained
  5. customis purified by chromatography under an argon pressure of 50 kPa
  6. washon a column of silica gel (particle size 40-60 μm; diameter 4 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume)
  7. additionThe fractions containing the expected product
  8. customevaporated under reduced pressure (2 kPa; 40° C.)
  9. customafter drying (90 Pa; 40° C.)

Sources & evidence

ORD record
ord-47b09e01d65245ffa81082ab7ec8598f
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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