Pyridine → 5-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

HRID 245631Notes

Reaction equation

HRID 245631 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[C:17]([N:22]2[C:26]([C:27](O)=O)=[CH:25][C:24]([O:30][CH3:31])=[N:23]2)=[N:18][CH:19]=[CH:20][CH:21]=1.N1C=CC=CC=1.CS(Cl)(=O)=O>O1CCCC1>[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:27]([C:26]1[N:22]([C:17]3[C:16]([Cl:15])=[CH:21][CH:20]=[CH:19][N:18]=3)[N:23]=[C:24]([O:30][CH3:31])[CH:25]=1)[O:12][C:11]2=[O:13]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 509892861-(3-chloropyridin-2-yl)-3-methoxy-1H-pyrazole-5-carboxylic acidHCID 57990137HCID 57990137, compound

Product 1

HCID 579901685-chloro-7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 400 mg (1.89 mmol) of 6-amino-5-chloro-1H-indazole-7-carboxylic acid in 16 mL of anhydrous tetrahydrofuran is added 479 mg (1.89 mmol) of 2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carboxylic acid followed by 684 μL (8.50 mmol) of pyridine. The mixture is stirred at ambient temperature during 30 minutes. Then the suspension is cooled to 0° C. and 516 μL (6.66 mmol) of methanesulfonyl chloride are added dropwise. The mixture is stirred at ambient temperature for 5 hours. Then the solvent is evaporated and the residue is triturated with a minimum of cold water. The precipitate, which is formed is filtrated and washed with cold water. The pale yellowish product obtained (870 mg) is engaged in the next step; LC/MS:530/532 (M+H)+.

Workup

  1. temperatureThen the suspension is cooled to 0° C.
  2. stirringThe mixture is stirred at ambient temperature for 5 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. customThe pale yellowish product obtained (870 mg)

Sources & evidence

ORD record
ord-a82ae4feee814f6f9a06ab37245a3c55
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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