Trifluoroacetic acid → HCID 59363718, compound

HRID 1094771Notes

Reaction equation

HRID 1094771 reaction equation
CC(OC([NH:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=O)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[C:10]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:12]([CH3:15])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 59363634HCID 59363634, compound

Product 1

HCID 59363718HCID 59363718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Methyl 3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-pyridinecarboxylate D34 (1.3 g) was dissolved in DCM (80 ml) and the mixture stirred at 0° C. A solution of TFA (5 ml, 64.9 mmol) in DCM (10 ml) was dropped into the cold mixture over 3 minutes. The resulting solution was left under stirring at 0° C. for 30 minutes, then the mixture was left still at room temperature overnight. TFA (4 ml, 51.9 mmol) dissolved in DCM (10 ml) was added over 3 minutes and the mixture stirred again at room temperature for 5 hours. The solution was loaded onto an SCX-25 g column, the column was eluted and after evaporation under reduced pressure of the solvent it was obtained the title compound D35 (770 mg) was obtained as a white solid. UPLC (Basic GEN_QC): rt=0.44 minutes, peak observed: 167 (M+1). C8H10N2O2 requires 166. 1H NMR (400 MHz, CDCl3) δ ppm 7.14 (d, 1 H), 7.01 (d, 1 H), 3.99 (s, 3 H), 2.52 (s, 3 H).

Workup

  1. waitThe resulting solution was left
  2. stirringunder stirring at 0° C. for 30 minutes
  3. additionwas added over 3 minutes
  4. stirringthe mixture stirred again at room temperature for 5 hours
  5. washthe column was eluted
  6. customafter evaporation under reduced pressure of the solvent it

Sources & evidence

ORD record
ord-36e37940a894447bbbc08499bf30440a
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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