Pyridine → 2-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,8-diaza-phenanthren-4-one

HRID 245646Notes

Reaction equation

HRID 245646 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([OH:14])=[O:13].[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>O1CCCC1>[Cl:15][C:16]1[C:17]([N:22]2[C:26]([C:27]3[O:13][C:12](=[O:14])[C:3]4[C:4]5[C:9](=[N:8][CH:7]=[CH:6][CH:5]=5)[CH:10]=[CH:11][C:2]=4[N:1]=3)=[CH:25][C:24]([C:30]([F:33])([F:31])[F:32])=[N:23]2)=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidHCID 205642906-Aminoquinoline-5-carboxylic acid

Product 1

HCID 579901052-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-3-oxa-1,8-diaza-phenanthren-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 240 mg (1.28 mmol) of 6-amino-quinoline-5-carboxylic acid in 9.60 mL of anhydrous tetrahydrofuran at 10° C., is added 372 mg (1.28 mmol) of 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid followed by 5134 (6.38 mmol) of pyridine. Then the suspension is cooled to 0° C. and 398 μL (5.10 mmol) of methanesulfonyl chloride are added dropwise. The mixture is stirred at ambient temperature for 48 hours. Then the solvent is evaporated and the residue is precipitated with a minimum of ethyl acetate and washed with ethyl acetate. After filtration, water is added to the filtrate and the new suspension formed is filtrated again. After drying on high vacuum pump 303 mg (54%) of solid are obtained; LC/MS:444/446 (M+H)+.

Workup

  1. customThen the solvent is evaporated
  2. customthe residue is precipitated with a minimum of ethyl acetate
  3. washwashed with ethyl acetate
  4. filtrationAfter filtration, water
  5. additionis added to the filtrate
  6. customthe new suspension formed
  7. filtrationis filtrated again
  8. dry with materialAfter drying on high vacuum pump 303 mg (54%) of solid
  9. customare obtained

Sources & evidence

ORD record
ord-ece83cf75b9348218d3a32a75c2a55d7
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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