Isopropylamine → HCID 86759455, compound

HRID 352533Notes

Reaction equation

HRID 352533 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[CH3:30])=[O:12])[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:44]([NH2:47])([CH3:46])[CH3:45].C(OCC)(=O)C>COC(C)(C)C>[CH3:45][CH:44]([NH:47][C:8]([C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][C:6]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:29])([C:21]([F:22])([F:23])[F:24])[C:25]([F:28])([F:27])[F:26])=[CH:16][C:15]=1[CH3:30])=[O:12])=[O:10])[CH3:46]

Participants

6

Reactant 4

HCID 6363IsopropylamineHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 86759456HCID 86759456, compound

Product 1

HCID 86759455HCID 86759455, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

In 10 ml of t-butyl methyl ether was dissolved 500 mg of 2-chloro-4-[4-(heptafluoro-2-propyl)-2-methylphenyl]aminocarbonyl-3-pyridinecarboxylic acid, followed by adding thereto 340 mg of ok trifluoroacetic anhydride, and the resulting mixture was stirred at room temperature for 2 hours. After the disappearance of the starting material was confirmed by TLC, 330 mg of isopropylamine was added to the mixture, followed by stirring at room temperature for another 2 hours. After completion of the reaction, ethyl acetate was added and the reaction solution was washed successively with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography using ethyl acetate/n-hexane as an eluent, to obtain 460 mg of the desired compound as white crystals.

Workup

  1. additionby adding
  2. additionwas added to the mixture
  3. additionwas added
  4. washthe reaction solution was washed successively with water
  5. dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-e75d405f54a14029bc4423e7776144dc
Source dataset
uspto-grants-2004_06
Patent number
US06747041B1

Reaction notes

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