Trifluoroacetic acid → HCID 86680564, compound

HRID 1487396Notes

Reaction equation

HRID 1487396 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1([F:42])[CH2:14][CH2:13][CH:12]([N:15]([C:22]2[CH:34]=[C:33]([N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)[CH:32]=[CH:31][C:23]=2[C:24]([O:26]C(C)(C)C)=[O:25])[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:11][CH2:10]1>ClCCl.C(OCC)(=O)C.C(OCC)C>[F:42][C:9]1([F:8])[CH2:14][CH2:13][CH:12]([N:15]([C:22]2[CH:34]=[C:33]([N:35]3[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]3)[CH:32]=[CH:31][C:23]=2[C:24]([OH:26])=[O:25])[C:16](=[O:21])[C:17]([F:18])([F:19])[F:20])[CH2:11][CH2:10]1

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86680565HCID 86680565, compound

Product 1

HCID 86680564HCID 86680564, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.62 ml (99 mmol) of trifluoroacetic acid is added to 2.5 g (4.95 mmol) of tert-butyl 2-(N-(4,4-difluorocyclohexyl)-2,2,2-trifluoroacetamido)-4-(4-methylpiperazin-1-yl)benzoate dissolved in 30 ml of dichloromethane. The reaction is left under stirring at room temperature overnight. The solvent is evaporated and then the crude reaction product is redissolved in 30 ml of ethyl acetate. The solvents are evaporated, the solid formed is redissolved in ethyl ether and the solvent is evaporated again. This operation is repeated three times until a light brown solid is obtained. 2.2 g of 2-(N-(4,4-difluorocyclohexyl)-2,2,2-trifluoroacetamido)-4-(4-methylpiperazin-1-yl)benzoic acid in the form of a trifluoroacetic salt is obtained (yield=79%).

Workup

  1. waitThe reaction is left
  2. customThe solvent is evaporated
  3. customthe crude reaction product
  4. customThe solvents are evaporated
  5. customthe solid formed
  6. customthe solvent is evaporated again
  7. customis obtained

Sources & evidence

ORD record
ord-44c9c8226b5740cf985e5e4fbe6df79d
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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