Trifluoroacetic acid → N-(4-amino-2-methyl-6-(((1-methylethyl)amino)carbonyl)phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1268897Notes

Reaction equation

HRID 1268897 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([NH:15][C:16]3[C:21]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[CH:20][C:19]([N+:28]([O-])=O)=[CH:18][C:17]=3[CH3:31])=[O:14])=[CH:11][C:10]([C:32]([F:35])([F:34])[F:33])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl.[Zn]>[NH2:28][C:19]1[CH:20]=[C:21]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:16]([NH:15][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:32]([F:35])([F:34])[F:33])[CH:11]=2)=[O:14])=[C:17]([CH3:31])[CH:18]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18446929HCID 18446929, compound

Product 1

HCID 10227689N-(4-amino-2-methyl-6-(((1-methylethyl)amino)carbonyl)phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Zinc dust (90 mg, 1.4 mmol) was added to a solution of the product from Step C (70 mg, 0.14 mmole) and trifluoroacetic acid (2 mL) at 70° C. Some foaming occurred. After 10 minutes at 70° C., the mixture was cooled to 25° C., diluted with dichloromethane, and filtered. The filtrate was concentrated to remove most of the trifluoroacetic acid and the resulting residue was dissolved in acetonitrile (3 mL) and 1,2-dichloroethane (3 mL). The resulting solution was treated with strongly-basic ion exchange resin (Dowex® 550A, OH− form, 2 g), shaken for 1 hour and then filtered. Concentration of the filtrate gave the title compound, a compound of the invention, as a yellow solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customto remove most of the trifluoroacetic acid
  4. dissolutionthe resulting residue was dissolved in acetonitrile (3 mL)
  5. additionThe resulting solution was treated with strongly-basic ion exchange resin (Dowex® 550A, OH− form, 2 g)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-09eb3a8bbf834c1ebf7a9e6838cbca14
Source dataset
uspto-grants-2007_04
Patent number
US07199138B2

Reaction notes

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