Trifluoroacetic acid → HCID 21912819, compound

HRID 1245619Notes

Reaction equation

HRID 1245619 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:22]([O:31][CH3:32])=[N:23][N:24]([CH3:30])[C:25]=2[C:26]([F:29])([F:28])[F:27])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH3:32][O:31][C:22]1[C:21]([CH:18]2[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]2)=[C:25]([C:26]([F:28])([F:27])[F:29])[N:24]([CH3:30])[N:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86592098HCID 86592098, compound

Product 1

HCID 21912819HCID 21912819, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.0 mL) was added to a solution of 1-(tert-butoxycarbonyl-4-(3-methoxy-1-methyl-5-(trifluoromethyl)-(1H)-pyrazol-4-yl)piperidine (150 mg, 0.41 mmol, from Step D) in CH2Cl2 (3.0 mL). After 2 h, the reaction was concentrated and the residue was dissolved in EtOAc (15 mL) and washed with saturated aq. NaHCO3 (6 mL) followed by saturated aq. NaCl (5 mL). The organic layer was dried (Na2SO4), decanted, and evaporated to give the title compound as a white solid. For the title compound: 1H NMR (500 MHz, CD3OD) δ 3.89 (s, 3H), 3.80 (s, 3H), 3.32 (d, J=13, 2H), 2.95 (tt, J=13, 4, 1H), 2.93 (td, J=13, 3, 2H), 2.18 (qd, J=13, 4, 2H), 1.76 (d, J=13, 2H); ESI-MS 264.1 (M+H); HPLC A: 1.3 min.

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutionthe residue was dissolved in EtOAc (15 mL)
  3. washwashed with saturated aq. NaHCO3 (6 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customdecanted
  6. customevaporated

Sources & evidence

ORD record
ord-bf129b50378341f199c1a9e3efef0e17
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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