Butyryl chloride → HCID 22319518, compound

HRID 497716Notes

Reaction equation

HRID 497716 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[F:7][C:8]1[C:9]([C:18]([F:21])([F:20])[F:19])=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][N:14]=[C:13]2[NH2:17]>N1C=CC=CC=1>[F:7][C:8]1[C:9]([C:18]([F:21])([F:19])[F:20])=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][N:14]=[C:13]2[NH:17][C:1](=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 21939266HCID 21939266, compound

Product 1

HCID 22319518HCID 22319518, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
3 °C

Procedure

1.0 cm3 of butyryl chloride is added to 2.1 g of 7-fluoro-6-(trifluoromethyl)-1H-indazole-3-amine, prepared as in patent application WO 02/22608, 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 50 cm3 of ethyl acetate and 20 cm3 of water. The organic phase is washed with 2×20 cm3 of distilled water and then with 20 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 (60/40 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.), 875 mg of N-[7-fluoro-6-(trifluoromethyl)-1H-indazol-3-yl)butanamide are obtained in the form of a pink solid melting at 220°-222° C.

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure (2 kPa; 40° C.)
  2. washThe organic phase is washed with 2×20 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 (60/40 by volume)
  7. additionThe fractions containing the expected product
  8. customevaporated under reduced pressure (2 kPa; 40° C.)
  9. dry with materialafter drying (90 Pa; 40° C.), 875 mg of N-[7-fluoro-6-(trifluoromethyl)-1H-indazol-3-yl)butanamide

Sources & evidence

ORD record
ord-f2c3cb25591045f8a01f2ae6db1ec777
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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