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 1983073Notes

Reaction equation

HRID 1983073 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-9d1279655f4044c98ffb1af6556b9d0c
Source dataset
uspto-grants-2009_06
Patent number
US07541377B2

Reaction notes

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