Potassium Carbonate → HCID 67367913, compound

HRID 72799Notes

Reaction equation

HRID 72799 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([C:15](=O)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.[CH3:31][CH:32]1[CH2:36][CH2:35][CH2:34][N:33]1[C:37]([NH2:39])=[NH:38].C([O-])([O-])=O.[K+].[K+]>CC#N.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:38]=[C:37]([N:33]3[CH2:34][CH2:35][CH2:36][CH:32]3[CH3:31])[N:39]=[C:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 673697092-Methyl-pyrrolidine-1-carboxamidine trifluoroacetateHCID 67369974HCID 67369974, compound

Product 1

HCID 67367913HCID 67367913, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(4-fluoro-benzoyl)-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.20 g, 0.62 mmol) and 2-methyl-pyrrolidine-1-carboxamidine trifluoroacetate (0.14 g, 0.58 mmol) in MeCN (3 mL) was added K2CO3 (0.190 g, 1.4 mmol). The mixture was heated at reflux for 15 h, then cooled to rt, diluted with H2O and extracted with CH2Cl2 (2×). The combined organic extracts were dried and concentrated. The residue was purified by FCC to give the title compound (0.193 g, 81%) as a clear oil. MS (ESI): mass calcd. for C23H23FN4O2, 412.5; m/z found, 413.4 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 h
  3. extractionextracted with CH2Cl2 (2×)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-3b06a4301de144408594c52fd84936a0
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

Loading…