Ammonia → HCID 22319519, compound

HRID 497631Notes

Reaction equation

HRID 497631 reaction equation
[Br:1][C:2]1[C:10]([N+:11]([O-])=O)=[C:9]2[C:5]([C:6]([NH:14][C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[N:7][NH:8]2)=[CH:4][CH:3]=1.N>O.C(O)C>[Br:1][C:2]1[C:10]([NH2:11])=[C:9]2[C:5]([C:6]([NH:14][C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 10064982HCID 10064982, compound

Product 1

HCID 22319519HCID 22319519, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

4.25 g of ferrous sulphate heptahydrate dissolved in 25 cm3 of water are added dropwise to 510 mg of N-[6-bromo-7-nitro-1H-indazol-3-yl]butanamide, described in Example 29, in 20 cm3 of ethanol cooled to about 5° C. The temperature rises to about 28° C., the mixture is left stirring for 30 minutes, 5.2 cm3 of 28% aqueous ammonia are then added, the mixture is refluxed for 2 hours, a further 2×1.5 cm3 of 28% aqueous ammonia are then added and the mixture is left stirring for a further 10 minutes and filtered while hot through a sinter funnel packed with Celite. The precipitate is rinsed with 20 cm3 of methanol and the filtrate is concentrated to dryness under reduced pressure (2 kPa; 40° C.). The residue is taken up in 50 cm3 of ethyl acetate and washed with 25 cm3 of saturated sodium hydrogen carbonate solution and then with 25 cm3 of saturated sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate and concentrated under reduced pressure (2 kPa; 40° C.). After drying (90 Pa; 50° C.), 55 mg of N-[6-bromo-7-amino-1H-indazol-3-yl]butanamide are thus obtained in the form of a mauve-coloured solid.

Workup

  1. customrises to about 28° C.
  2. waitthe mixture is left
  3. temperaturethe mixture is refluxed for 2 hours
  4. waitthe mixture is left
  5. stirringstirring for a further 10 minutes
  6. filtrationfiltered while hot through a sinter funnel
  7. washThe precipitate is rinsed with 20 cm3 of methanol
  8. concentrationthe filtrate is concentrated to dryness under reduced pressure (2 kPa; 40° C.)
  9. washwashed with 25 cm3 of saturated sodium hydrogen carbonate solution
  10. customThe organic phase is separated out
  11. dry with materialdried over magnesium sulphate
  12. concentrationconcentrated under reduced pressure (2 kPa; 40° C.)
  13. dry with materialAfter drying (90 Pa; 50° C.), 55 mg of N-[6-bromo-7-amino-1H-indazol-3-yl]butanamide
  14. customare thus obtained in the form of a mauve-coloured solid

Sources & evidence

ORD record
ord-07e1c6cd3cae4c38b6b974d1d7ec1769
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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