Trifluoroacetic acid → HCID 68276432, compound

HRID 1048788Notes

Reaction equation

HRID 1048788 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1([F:16])[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.[NH2:35][C:36]1[CH:48]=[C:47]([N:49]2[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]2)[CH:46]=[CH:45][C:37]=1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>ClCCl.C(OCC)(=O)C>[F:8][C:9]1([F:16])[CH2:14][CH2:13][CH:12]([NH:35][C:36]2[CH:48]=[C:47]([N:49]3[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]3)[CH:46]=[CH:45][C:37]=2[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 157890924,4-DifluorocyclohexanoneHCID 667359202-Amino-4-(4-methylpiperazin-1-yl) benzoic acid tertbutyl ester

Product 1

HCID 68276432HCID 68276432, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.045 ml (13.57 mmol) of trifluoroacetic acid, 1 g (7.46 mmol) of 4,4-difluorocyclohexanone and 2.158 g (8.20 mmol) of tetramethylammonium triacetoxyborohydride are added to 1.521 g (5.22 mmol) of tert-butyl 2-amino-4-(4-methylpiperazin-1-yl)benzoate dissolved in 60 ml of dichloromethane. The reaction is left under stirring at room temperature for 24 hours. The solvent is evaporated and then the crude reaction product is redissolved in 30 ml of ethyl acetate. The solution is successively washed with 0.5 M HCl solution, 0.5 M soda solution and finally with saturated NaHCO3 solution. The organic phase is dried on sodium sulfate, filtered and concentrated to obtain 2.2 g of tert-butyl 2-(4,4-difluorocyclohexylamino)-4-(4-methylpiperazin-1-yl)benzoate in the form of a light brown gum (yield=72%).

Workup

  1. waitThe reaction is left
  2. customThe solvent is evaporated
  3. customthe crude reaction product
  4. washThe solution is successively washed with 0.5 M HCl solution, 0.5 M soda solution and finally with saturated NaHCO3 solution
  5. customThe organic phase is dried on sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-25e5fce02d024a409ce2297d84202896
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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