Ammonia → 5-(3-Chloro-5-fluorophenyl)-1-(6-aminopyridin-3-yl)-1H-pyrazole-3-carboxylic acid

HRID 930004Notes

Reaction equation

HRID 930004 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[N:16][C:17](Cl)=[CH:18][CH:19]=3)[N:12]=[C:11]([C:21]([OH:23])=[O:22])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[NH3:24]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:15]=[N:16][C:17]([NH2:24])=[CH:18][CH:19]=3)[N:12]=[C:11]([C:21]([OH:23])=[O:22])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 89610057HCID 89610057, compound

Product 1

HCID 896024655-(3-Chloro-5-fluorophenyl)-1-(6-aminopyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Procedure

70 mg (80%, 0.16 mmol) of the compound of Example 23A is mixed with ammonia solution (14 N, 1.5 ml) and kept in the microwave in a sealed tube for 13 hours at 150° C., whereby a pressure of 20 bar develops. After cooling to room temperature, the ammonia solution is removed i. vac., and the residue is purified via preparative HPLC (mobile solvent: acetonitrile/water gradient). 20 mg (38% of theory) of the title compound is obtained.

Workup

  1. customthe ammonia solution is removed i
  2. custom, and the residue is purified via preparative HPLC (mobile solvent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-21032a3783f34321b82af8f89f4a3ce8
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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