Trifluoroacetic acid → HCID 63761213, compound

HRID 2239589Notes

Reaction equation

HRID 2239589 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-4085071e018744dd94c5aa5dcb2cd68a
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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