Dimethylformamide → 4-[3-(3-Trifluoromethyl-benzoylamino)-benzo[1,2,4]triazin-7-yloxy]-pyridine-2-carboxylic acid methyl amide trifluoroacetate salt

HRID 387429Notes

Reaction equation

HRID 387429 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:22]=[CH:21][C:15]3[N:16]=[C:17]([NH2:20])[N:18]=[N:19][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].C([O:27][K])(C)(C)C.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](Cl)=[O:35].CN(C)[CH:44]=[O:45]>>[F:29][C:30]([F:41])([F:40])[C:44]([OH:45])=[O:27].[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:22]=[CH:21][C:15]3[N:16]=[C:17]([NH:20][C:34](=[O:35])[C:33]4[CH:37]=[CH:38][CH:39]=[C:31]([C:30]([F:29])([F:40])[F:41])[CH:32]=4)[N:18]=[N:19][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 591353294-((3-Aminobenzo[e][1,2,4]triazin-7-yl)oxy)-N-methylpicolinamideHCID 178418922HCID 178418922, compound

Product 1

HCID 866042844-[3-(3-Trifluoromethyl-benzoylamino)-benzo[1,2,4]triazin-7-yloxy]-pyridine-2-carboxylic acid methyl amide trifluoroacetate salt

Conditions

Temperature
100 °C

Procedure

100 mg (0.337 mmol, 1.0 equivalent) of 4-(3-amino-benzo[1,2,4]triazin-7-yloxy)-pyridine-carboxylic acid methylamide were dissolved in 2 mL of anhydrous dimethylformamide with heating to about 100° C. 45.4 mg (0.405 mmol, 1.2 equivalent) of solid tert-BuOK was added to the solution. The resulting dark-red solution was stirred at 100° C. for 30 min, then it was allowed to cool down to ambient temperature. 84.5 mg (0.405 mmol, 1.2 equivalent) of 3-trifluoromethyl-benzoyl chloride was added to the mixture via a syringe. It was allowed to stir at ambient temperature for 2 hours. The reaction mixture was filtered through 0.22μ syringe filter and purified by reverse-phase prep-HPLC using acetonitrile/water mixture with 0.1% of TFA.

Workup

  1. temperatureto cool down to ambient temperature
  2. stirringto stir at ambient temperature for 2 hours
  3. filtrationThe reaction mixture was filtered through 0.22μ syringe
  4. filtrationfilter
  5. custompurified by reverse-phase

Sources & evidence

ORD record
ord-4a1f2f25120c47689d699a0711d673b4
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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