Pyridine → 4-chloro-6-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-7-oxa-2-thia-1,3,5-triaza-cyclopenta[b]naphthalen-8-one

HRID 2039608Notes

Reaction equation

HRID 2039608 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:5]2=[N:6][S:7][N:8]=[C:4]2[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]([C:30]([F:33])([F:32])[F:31])=[N:23]2)=[N:18][CH:19]=[CH:20][CH:21]=1.N1C=CC=CC=1.CS(Cl)(=O)=O>C(#N)C>[Cl:14][C:3]1[C:4]2[C:5](=[N:6][S:7][N:8]=2)[CH:9]=[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]([C:30]([F:33])([F:31])[F:32])[CH:25]=1)[O:12][C:11]2=[O:13]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidHCID 578559746-Amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acid

Product 1

HCID 578559084-chloro-6-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-7-oxa-2-thia-1,3,5-triaza-cyclopenta[b]naphthalen-8-oneYield 92.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 300 mg (1.31 mmol) of 6-amino-7-chloro-benzo[1,2,5]thiadiazole-5-carboxylic acid in 12 ml of acetonitrile, is added 381 mg (1.31 mmol) of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid followed by 0.47 ml (5.88 mmol) of pyridine. The mixture is stirred at ambient temperature during 30 min. Then the suspension is cooled at a temperature of 0° C. and 0.36 ml (4.57 mmol) of methanesulfonyl chloride is added dropwise. The mixture is stirred at a temperature of 0° C. during 30 min and 2 hours at ambient temperature. Then the solvent is evaporated and the residue is precipitated in a minimum of cold H2O. After filtration and washing of the solid with a minimum of cold H2O, 585 mg (1.21 mmol, 92%) of a dark violet solid is obtained. LC/MS: 485/487 (M+1)+.

Workup

  1. additionis added dropwise
  2. stirringThe mixture is stirred at a temperature of 0° C. during 30 min and 2 hours at ambient temperature
  3. customThen the solvent is evaporated
  4. customthe residue is precipitated in a minimum of cold H2O
  5. filtrationAfter filtration
  6. washwashing of the solid with a minimum of cold H2O

Sources & evidence

ORD record
ord-477ab6fa3fb5466c8c2d73be2a8f98e7
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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