Trifluoroacetic acid → HCID 21306951, compound

HRID 926536Notes

Reaction equation

HRID 926536 reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]([F:32])([F:31])[C:10]1[CH:30]=[CH:29][C:13]([C:14]([CH:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)=[O:15])=[CH:12][N:11]=1>C(Cl)Cl>[NH:19]1[CH2:20][CH2:21][CH:16]([C:14]([C:13]2[CH:12]=[N:11][C:10]([C:9]([F:32])([F:8])[F:31])=[CH:30][CH:29]=2)=[O:15])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118005538HCID 118005538, compound2×

Product 1

HCID 21306951HCID 21306951, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (34.4 mL, 449.3 mmol) was added to a solution of tert-butyl 4-(6-(trifluoromethyl)nicotinoyl)piperidine-1-carboxylate (Intermediate 56: step b, 16.1 g, 44.9 mmol) in DCM (450 mL) and the resulting solution was stirred at room temperature for 3 hours. The mixture was concentrated to remove most of the TFA on the rotary evaporator and a mixture of EtOAc/hexanes was added. The white solid that precipitated was filtered and dried to provide the title compound which was used in the next step without purification.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove most of the TFA on the rotary evaporator
  3. additiona mixture of EtOAc/hexanes
  4. additionwas added
  5. customThe white solid that precipitated
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-64b009ee9ede4520b6b22acd0c6e5fbf
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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