Butyryl chloride → HCID 10423871, compound

HRID 497599Notes

Reaction equation

HRID 497599 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([NH2:17])=[N:13][NH:14]2)=[CH:10][CH:9]=1>N1C=CC=CC=1>[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([NH:17][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[N:13][NH:14]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 27866316-bromo-1H-indazol-3-amine

Product 1

HCID 10423871HCID 10423871, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

0.24 cm3 of butyryl chloride is added to 500 mg of 6-bromo-1H-indazole-3-amine described previously in Example 12, in 15 cm3 of pyridine, and cooled to about 5° C. The reaction medium is allowed to return to about 19° C. over 50 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 and filtered to give after drying (90 Pa; 50° C.), 356 mg of N-[6-bromo-1H-indazol-3-yl]butanamide in the form of an off-white solid melting at 202° C.

Workup

  1. customThe reaction medium is evaporated under reduced pressure (2 kPa; 50° C.)
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered through a sinter funnel
  4. customevaporated under reduced pressure (2 kPa; 50° C.)
  5. filtrationfiltered
  6. customto give
  7. dry with materialafter drying (90 Pa; 50° C.), 356 mg of N-[6-bromo-1H-indazol-3-yl]butanamide in the form of an off-white solid melting at 202° C.

Sources & evidence

ORD record
ord-c95d221832b5426a9db11709bb95782d
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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