Trifluoroacetic acid → HCID 86692633, compound

HRID 1748684Notes

Reaction equation

HRID 1748684 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:21][CH2:20][CH2:19][CH:18]([C:22]2[C:27]([CH2:28]C)=[CH:26][C:25]([NH:30][C:31]([C:33]3[CH:34]=[N:35][N:36]([C:39]4[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][N:40]=4)[C:37]=3[CH3:38])=[O:32])=[CH:24][N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.[OH-].[Na+]>ClCCl>[NH:15]1[CH2:21][CH2:20][CH2:19][CH:18]([C:22]2[N:23]=[CH:24][C:25]([NH:30][C:31]([C:33]3[CH:34]=[N:35][N:36]([C:39]4[CH:44]=[CH:43][C:42]([C:45]([F:47])([F:46])[F:48])=[CH:41][N:40]=4)[C:37]=3[CH3:38])=[O:32])=[CH:26][C:27]=2[CH3:28])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86692634HCID 86692634, compound

Product 1

HCID 86692633HCID 86692633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.0 ml) was added at room temperature to a solution of 4-[3-ethyl-5-({5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carbonyl}amino)pyridin-2-yl]azepan-1-carboxylic acid tert-butyl ester (1.1 g) described in Example D291 in dichloromethane (20 ml), and stirred at the same temperature for 4 hours. After completion of the reaction, 4N aqueous solution of sodium hydroxide was added to adjust the solution to pH 11 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated to give N-[6-(azepan-4-yl)-5-methylpyridin-3-yl]-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide as a pale yellow oil.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3901105c22444780b665ae13c0737a4e
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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