Pyridine → HCID 57990091, compound

HRID 245628Notes

Reaction equation

HRID 245628 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[Cl:14].[Cl:15][C:16]1[CH:17]=[C:18]([C:28](O)=O)[N:19]([C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=2)[N:20]=1.N1C=CC=CC=1.CS(Cl)(=O)=O>C(#N)C>[Cl:14][C:3]1[CH:4]=[C:5]2[CH:6]=[N:7][NH:8][C:9]2=[C:10]2[C:2]=1[N:1]=[C:28]([C:18]1[N:19]([C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][N:22]=3)[N:20]=[C:16]([Cl:15])[CH:17]=1)[O:12][C:11]2=[O:13]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 211073323-Chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxylic acidHCID 57990137HCID 57990137, compound

Product 1

HCID 57990091HCID 57990091, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1.00 g (4.58 mmol) of 6-amino-5-chloro-1H-indazole-7-carboxylic acid in 40 mL of anhydrous acetonitrile is added 1.18 g (4.58 mmol) of 5-chloro-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid followed by 1.7 mL (20.6 mmol) of pyridine. The mixture is stirred at ambient temperature during 30 minutes. Then the suspension is cooled to 0° C. and 1.25 mL (16.0 mmol) of methanesulfonyl chloride is added dropwise. The mixture is stirred at ambient temperature for 6 hours. Then the solvent is evaporated and the residue is triturated with a minimum of cold water. The precipitate, which is formed is filtrated, washed with cold water and dried. Purification by flash chromatography (SiO2, toluene/methylene chloride/ethyl acetate 10:10:3) affords 910 mg (39%) of the product as a yellowish solid; LC/MS:433/435 (M+H)+.

Workup

  1. temperatureThen the suspension is cooled to 0° C.
  2. stirringThe mixture is stirred at ambient temperature for 6 hours
  3. customThen the solvent is evaporated
  4. customthe residue is triturated with a minimum of cold water
  5. customThe precipitate, which is formed
  6. filtrationis filtrated
  7. washwashed with cold water
  8. customdried
  9. customPurification by flash chromatography (SiO2, toluene/methylene chloride/ethyl acetate 10:10:3)

Sources & evidence

ORD record
ord-21f02aee34d5430a9d5a187fd3eb570f
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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