Trifluoroacetic acid → HCID 57418407, compound

HRID 1868125Notes

Reaction equation

HRID 1868125 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([N:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C@H:10]([CH3:40])[CH2:9]2)=[C:4]([C:41]([F:44])([F:43])[F:42])[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([N:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)=[CH:19][CH:18]=3)(=[O:15])=[O:16])[C@H:10]([CH3:40])[CH2:9]2)=[C:4]([C:41]([F:44])([F:42])[F:43])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68551030HCID 68551030, compound

Product 1

HCID 57418407HCID 57418407, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL flask containing tert-butyl 4-[4-({(2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazin-1-yl}sulfonyl)-1-naphthyl]piperazine-1-carboxylate (185.2 mg) and 5 mL of CH2Cl2 was added 3 mL of TFA. This was stirred at room temperature for 4.5 hr. Reaction was complete as determined by TLC. Solvent and TFA was removed under vacuum. The resulting residue was dissolved in CH2Cl2, washed with sat. K2CO3 until pH=8, then washed with saturated brine, dried over Na2SO4 and concentrated down to yield (2R)-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methyl-1-[(4-piperazin-1-yl-1-naphthyl)sulfonyl]piperazine as a yellow solid (136.3 mg, 87.3% yield). HRMS: calcd for C26H28F4N4O2S+H+, 537.19418. found (ESI-FTMS, [M+H]1+), 537.1968. HPLC Method 1: room temperature, 5.003 min, 94.44%, HPLC Method 2: room temperature, 6.254 min, 93.74%.

Workup

  1. customReaction
  2. customSolvent and TFA was removed under vacuum
  3. dissolutionThe resulting residue was dissolved in CH2Cl2
  4. washwashed with sat. K2CO3 until pH=8
  5. washwashed with saturated brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated down

Sources & evidence

ORD record
ord-ead7dccb40724c6a8137ae1a9b78db9e
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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