Trifluoroacetic acid → HCID 86680564, compound

HRID 1048789Notes

Reaction equation

HRID 1048789 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-99ce4116c9a14b9f98f078babd4dc0f9
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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