Trifluoroacetic acid → HCID 63761213, compound

HRID 2421992Notes

Reaction equation

HRID 2421992 reaction equation
[Cl:1][C:2]1[C:3]([N:12]2[CH2:15][CH:14]([NH:16]C(=O)OC(C)(C)C)[CH2:13]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([N:12]2[CH2:13][CH:14]([NH2:16])[CH2:15]2)=[N:4][CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86625879HCID 86625879, compound

Product 1

HCID 63761213HCID 63761213, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]azetidin-3-yl}carbamate (0.85 g, 2.42 mmol) was dissolved in DCM (4 mL) and TFA (3 mL) and stirred at rt for 1 h. The mixture was concentrated and redissolved in EtOAc, washed with saturated aqueous K2CO3. The organic layer was dried with Na2SO4, filtered and evaporated affording the title compound (0.58 g, 95.1%). 1H NMR (500 MHz, CDCl3): δ 1.65 (bs, 2H), 3.91-3.98 (m, 3H), 4.57-4.61 (m, 2H), 7.58 (s, 1H), 8.26 (s, 1H); 13C NMR (125 MHz, CDCl3): δ 43.68, 63.02, 115.38, 116.90 (q, JC-F=33.2 Hz), 123.91 (q, JC-F=270.9 Hz), 134.95, 143.76, 157.56; Mass Spectrum: M+H+ 252.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in EtOAc
  3. washwashed with saturated aqueous K2CO3
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-503b4b05e126417b99253d57e9583410
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

Loading…