Pyridine → HCID 57855892, compound

HRID 887737Notes

Reaction equation

HRID 887737 reaction equation
[NH2:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([OH:14])=[O:13])[N:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:6]=[CH:5]2.[Cl:20][C:21]1[C:22]([N:27]2[C:31]([C:32](O)=O)=[CH:30][C:29]([C:35]([F:38])([F:37])[F:36])=[N:28]2)=[N:23][CH:24]=[CH:25][CH:26]=1.N1C=CC=CC=1.CS(Cl)(=O)=O>C(#N)C.CCCCCC.C(OCC)(=O)C>[Cl:20][C:21]1[C:22]([N:27]2[C:31]([C:32]3[O:13][C:12](=[O:14])[C:11]4[C:2](=[C:3]([CH3:19])[C:4]5[C:9]([CH:10]=4)=[N:8][C:7]([C:15]([F:18])([F:16])[F:17])=[CH:6][CH:5]=5)[N:1]=3)=[CH:30][C:29]([C:35]([F:38])([F:36])[F:37])=[N:28]2)=[N:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 113921841-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acidHCID 57855894HCID 57855894, compound

Product 1

HCID 57855892HCID 57855892, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 6-amino-5-methyl-2-trifluoromethyl-quinoline-7-carboxylic acid (0.60 g), 2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid (0.65 g, example 2, step 2) and pyridine (0.79 g) in acetonitrile (30 mL) is cooled to 0-5° C. and treated drop wise with methane sulfonyl chloride (0.89 g) dissolved in 2 mL acetonitrile. TLC analysis (hexane/ethyl acetate 4:1) after 2 h shows reaction completion. The reaction mixture is concentrated to ⅔ of the original volume in vacuum and poured onto 75 mL of ice/water. The resultant crystals are filtered off, washed with water and dried in vacuum to give 1.0 g of the title compound of the formula

Workup

  1. customreaction completion
  2. concentrationThe reaction mixture is concentrated
  3. additionpoured onto 75 mL of ice/water
  4. filtrationThe resultant crystals are filtered off
  5. washwashed with water
  6. customdried in vacuum

Sources & evidence

ORD record
ord-659a4c1696224b569dc17dd8813dc220
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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