Butyryl chloride → N-[5-(trifluoromethyl)-1H-indazol-3-yl]butanamide

HRID 497597

Reaction equation

HRID 497597 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[F:7][C:8]([F:20])([F:19])[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[NH2:18]>N1C=CC=CC=1>[F:20][C:8]([F:7])([F:19])[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[NH:18][C:1](=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 16736Bay-H-1127

Product 1

HCID 10378475N-[5-(trifluoromethyl)-1H-indazol-3-yl]butanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.26 cm3 of butyryl chloride is added to 500 mg of 5-(trifluoromethyl)-1H-indazole-3-amine, prepared according to patent U.S. Pat. No. 3,133,081, in 15 cm3 of pyridine, and cooled to about 5° C. The reaction medium is allowed to return to about 19° C. over 12 hours. The reaction medium is 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 taken up in 15 cm3 of dichloromethane, filtered and dried under reduced pressure (90 Pa; 50° C.) to give 390 mg of N-[5-(trifluoromethyl)-1H-indazol-3-yl]butanamide in the form of an off-white solid melting at 230° C.

Workup

  1. customprepared
  2. customThe reaction medium is evaporated under reduced pressure (2 kPa; 50° C.)
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered through a sinter funnel
  5. customevaporated under reduced pressure (2 kPa; 50° C.)
  6. filtrationfiltered
  7. customdried under reduced pressure (90 Pa; 50° C.)

Sources & evidence

ORD record
ord-beba78b9880f44de8bb9822551b1b2fb
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Linked notes

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