Trifluoroacetic acid → 2-Methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one

HRID 1427156Notes

Reaction equation

HRID 1427156 reaction equation
C(OC([C:6]1[C:7]([CH:13]2[CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15][N:14]2[C:26]([O:28]C(C)(C)C)=O)=[N:8][C:9]([CH3:12])=[CH:10][CH:11]=1)=O)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:12][C:9]1[CH:10]=[CH:11][C:6]2[C:26](=[O:28])[N:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH:13]3[C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68176488Bis(1,1-Dimethylethyl) 2-{3-[(ethyloxy)carbonyl]-6-methyl-2-pyridinyl}-1,4-piperazinedicarboxylate2×

Product 1

HCID 705575122-Methyl-8,9,10,10a-tetrahydropyrido[2',3':3,4]pyrrolo[1,2-a]pyrazin-5(7H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bis(1,1-dimethylethyl) 2-{3-[(ethyloxy)carbonyl]-6-methyl-2-pyridinyl}-1,4-piperazinedicarboxylate (may be prepared as described in Intermediate 5; 4.96 g) in dichloromethane (200 mL) was cooled to 0° C. and then TFA (20 mL, 260 mmol) was added. This was allowed to warm to room temperature then stirred for 4 hours. The reaction mixture was redissolved in DCM (100 ml), then TFA (10 ml) added and the whole stirred at room temperature for 1.5 hours. The reaction mixture was fully evaporated and azeotroped with toluene. This was dissolved in methanol (200 mL) and then potassium carbonate (3.05 g) was added and the mixture heated to reflux for 8 hours. The methanol was evaporated and then the residue was partitioned between EtOAc and water. The organic layer was then washed with water and then brine, dried through a hydrophobic frit and then evaporated to an orange oil (87 mg), which was found to be impurities.

Workup

  1. stirringthe whole stirred at room temperature for 1.5 hours
  2. customThe reaction mixture was fully evaporated
  3. customazeotroped with toluene
  4. dissolutionThis was dissolved in methanol (200 mL)
  5. additionpotassium carbonate (3.05 g) was added
  6. temperaturethe mixture heated
  7. temperatureto reflux for 8 hours
  8. customThe methanol was evaporated
  9. customthe residue was partitioned between EtOAc and water
  10. washThe organic layer was then washed with water
  11. dry with materialbrine, dried through a hydrophobic frit
  12. customevaporated to an orange oil (87 mg), which

Sources & evidence

ORD record
ord-5e0bdf80309048e282bc2c9833145d22
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

Loading…