Trifluoroacetic acid → HCID 11711456, compound

HRID 2113695Notes

Reaction equation

HRID 2113695 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:33][C@@H:34]1[CH2:38][CH2:37][O:36][CH2:35]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:33][C@@H:34]1[CH2:38][CH2:37][O:36][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11548129HCID 11548129, compound

Product 1

HCID 11711456HCID 11711456, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a vial was added tert-butyl 4-[4-(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)phenyl]piperazine-1-carboxylate (20.0 mg, 0.0384 mmol) and 1 mL of a 20% (v/v) solution of TFA in CH2Cl2. The reaction was stirred at room temperature for 1 hour and then the solvent was removed under reduced pressure. The residue was dissolved in 10 mL of ethyl acetate and washed once with 10 mL of saturated aqueous NaHCO3. The organic layer was then dried over sodium sulfate and concentrated under reduced pressure to give 13 mg (0.0309 mmol, 80%) of 1-[4-(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)phenyl]piperazine as a yellow oil. LC/MS (EI) tR 2.02 (Method C), m/z 421.2 (M++1). 1H NMR (CDCl3 300 MHz) δ 1.9 (m, 4H); 3.0 (d, 4H); 3.1 (d, 4H); 3.7-3.9 (m, 3H); 3.8 (s, 3H); 4.6 (m, 1H); 6.4 (s, 1H); 6.5 (s, 1H); 6.8 (m, 3H); 7.0 (d, 1H); 7.2 (d, 2H); 7.7 (s, 1H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 10 mL of ethyl acetate
  3. washwashed once with 10 mL of saturated aqueous NaHCO3
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f68d807289a4426bdc2f59688f245d5
Source dataset
uspto-grants-2008_10
Patent number
US07432266B2

Reaction notes

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