Trifluoroacetic acid → 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine

HRID 573866Notes

Reaction equation

HRID 573866 reaction equation
[F:1][C:2]([F:32])([F:31])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:30]=[CH:29][C:18]([CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.FC(F)(F)C(O)=O>ClCCl>[F:32][C:2]([F:1])([F:31])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:30]=[CH:29][C:18]([CH2:19][CH2:20][NH2:21])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90404063tert-butyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethylcarbamate

Product 1

HCID 904040382-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamineYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of tert-butyl 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethylcarbamate (C50) (0.10 g, 0.22 mmol) in dichloromethane (1.6 mL) was added trifluoroacetic acid (0.19 mL, 0.25 mmol), and the solution was allowed to warm slowly to ambient temperature and stirred overnight. The reaction mixture was concentrated, taken up in hexanes, and concentrated until a solid was obtained. The solid was dissolved in dichloromethane and washed with saturated sodium bicarbonate. The aqueous layer was extracted with dichloromethane (2×). The combined organic layers were washed with saturated sodium bicarbonate. The organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title compound as a white solid (0.075 g, 97%): 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.18-8.07 (m, 2H), 7.83-7.74 (m, 2H), 7.41-7.29 (m, 4H), 3.02 (t, J=6.8 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 1.45-1.29 (m, 2H); 19F NMR (376 MHz, CDCl3) δ −58.04.

Workup

  1. stirringstirred overnight
  2. concentrationThe reaction mixture was concentrated
  3. concentrationconcentrated until a solid
  4. customwas obtained
  5. washwashed with saturated sodium bicarbonate
  6. extractionThe aqueous layer was extracted with dichloromethane (2×)
  7. washThe combined organic layers were washed with saturated sodium bicarbonate
  8. dry with materialThe organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-683cd6c9ddc04e23b779279361ba1b81
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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