Potassium Carbonate → HCID 46917071, compound

HRID 2045913Notes

Reaction equation

HRID 2045913 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1.C([O-])([O-])=O.[K+].[K+].[N-]=C=O>CC#N.C(OCC)(=O)C>[N:22]1([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[CH:21]=[N:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH:7]=2)=[O:4])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 105034IsocyanateHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 46917071HCID 46917071, compoundYield 40.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (100 mg, 0.336 mmol), pyrrolidine (34 μL, 0.403 mmol) and K2CO3 (112 mg, 0.806 mmol) in MeCN (5 mL) was stirred at 50° C. for 18 hrs. HPLC analysis still showed starting material and therefore, the reaction mixture was further stirred at 100° C. for 1 h to afford completion. The mixture was cooled to room temperature and ethyl acetate (20 mL) was added, the organic phase was washed with water (20 mL) and then brine (20 mL), and dried over MgSO4, and solvent evaporated. The resulting oily solid was dissolved in DCM (5 mL) and stirred overnight with polystyrene methylisocyanate (“PS-isocyanate” 276 mg, 0.4 mmol, 1.46 mmol/g) to remove any excess pyrrolidine. The polymer was filtered and the organic phase was remove in vacuo, to afford 2-pyrrolidin-1-yl-N-(3-quinoxalin-2-ylphenyl)acetamide (45 mg, 40% yield). LCMS calculated for C20H20N4O (M+H): 333.41. found 333.21. 1H-NMR (DMSO-d6, 400 Mhz) δH: 9.95 (s, 1H), 9.51 (s, 1H), 8.55 (s, 1H), 8.20-8.14 (m, 2H), 8.08-8.02 (m, 1H), 7.95-7.82 (m, 3H), 7.58-7.50 (m, 1H), 3.40 (s, 2H), 2.65-2.55 (m, 4H), 1.85-1.75 (m, 4H).

Workup

  1. customto afford completion
  2. temperatureThe mixture was cooled to room temperature
  3. washthe organic phase was washed with water (20 mL)
  4. dry with materialbrine (20 mL), and dried over MgSO4, and solvent
  5. customevaporated
  6. dissolutionThe resulting oily solid was dissolved in DCM (5 mL)
  7. customto remove any excess pyrrolidine
  8. filtrationThe polymer was filtered
  9. customthe organic phase was remove in vacuo

Sources & evidence

ORD record
ord-a19e29fa55174fa1b4a7a2c30906ae46
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

Loading…