Trifluoroacetic acid → HCID 59504632, compound

HRID 2400595Notes

Reaction equation

HRID 2400595 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([NH:26]C(=O)OC(C)(C)C)=[CH:22][CH:21]=3)[N:16]=2)[CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=2)[N:5]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)[N:16]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59504668HCID 59504668, compound

Product 1

HCID 59504632HCID 59504632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (4-{5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazol-3-yl}phenyl)carbamate (Example 101, 1.0 g, 2.25 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (5 mL). The reaction mixture was stirred at rt for 1 h. The solvent was removed in vacuo and the residue was re-dissolved in ethyl acetate. After washing with saturated aqueous sodium bicarbonate, the solvent was removed and the title compound was obtained as an off-white solid (770 mg, 99%): 1H NMR (400 MHz, CDCl3) 8.00 (d, 2H), 7.13 (d, 2H), 7.07 (d, 2H), 6.76 (s, 1H), 6.73 (d, 2H), 5.40 (s, 2H), 3.92 (broad, 2H), 2.32 (s, 3H), 2.23 (s, 3H); ES-MS m/z 346, HPLC RT (Method D) 2.48 min.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was re-dissolved in ethyl acetate
  3. washAfter washing with saturated aqueous sodium bicarbonate
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-1e01e1bd56724f01867d1b8257827ade
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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