Trifluoroacetic acid → 4-[(3-Fluorophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamide

HRID 883801Notes

Reaction equation

HRID 883801 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([N:17]([CH3:39])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[C@@H:27]([CH3:38])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([N:17]([CH3:39])[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:30][CH2:29][NH:28][C@@H:27]([CH3:38])[CH2:26]4)=[CH:20][CH:19]=3)=[O:16])[CH2:13][CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 576995151,1-dimethylethyl (2S)-4-({4-[({4-[(3-fluorophenyl)amino]-1-piperidinyl}carbonyl)(methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate

Product 1

HCID 236344374-[(3-Fluorophenyl)amino]-N-methyl-N-(4-{[(3S)-3-methyl-1-piperazinyl]methyl}phenyl)-1-piperidinecarboxamideYield 102.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl (2S)-4-({4-[({4-[(3-fluorophenyl)amino]-1-piperidinyl}carbonyl) (methyl)amino]phenyl}methyl)-2-methyl-1-piperazinecarboxylate (D33) (9.337 g, 17.322 mmol) was dissolved in DCM (144 mL) and cooled in an ice bath. TFA (36 mL) was added slowly and the mixture was allowed to stir for 2.5 h under argon. The solvent was removed under vacuum and the residue partitioned between DCM and saturated aqueous NaHCO3. The organic layer was separated and the aqueous layer extracted twice with DCM. The combined organic extracts were dried and concentrated to give the title compound as a cream coloured foam (7.82 g). MS (ES): MH+ 440.3.

Workup

  1. temperaturecooled in an ice bath
  2. customThe solvent was removed under vacuum
  3. customthe residue partitioned between DCM and saturated aqueous NaHCO3
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted twice with DCM
  6. customThe combined organic extracts were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b640c8f11a84f528457f66f1fdbc806
Source dataset
uspto-grants-2012_08
Patent number
US08236953B2

Reaction notes

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