Potassium Carbonate → HCID 46916504, compound

HRID 2045939Notes

Reaction equation

HRID 2045939 reaction equation
Br[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].C(=O)([O-])[O-].[K+].[K+].[N:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1>C(#N)C>[N:28]1[CH:33]=[CH:32][C:31]([N:34]2[CH2:35][CH2:36][N:37]([CH2:2][C:3]([NH:5][C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([C:12]4[CH:21]=[N:20][C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:13]=4)[CH:7]=3)=[O:4])[CH2:38][CH2:39]2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 705171-(4-Pyridyl)piperazineHCID 46916455HCID 46916455, compound

Product 1

HCID 46916504HCID 46916504, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (100 mg, 0.292 mmol), potassium carbonate (51 mg, 0.365 mmol) and 1-(4-pyridyl)-piperazine (50 mg, 0.307 mmol) in acetonitrile (5 mL) was heated at reflux for 15 min. The solvent was evaporated in vacuo and the crude reaction mixture was purified by preparative LCMS to afford 2-(4-(pyridin-4-yl)piperazin-1-yl)-N-(3-(quinoxalin-2-yl)phenyl)acetamide (30 mg, 24% yield). LCMS calculated for C25H24N6O (M+H): 425.50. found 425.44. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.04 (1H, br.), 9.52 (1H, s), 8.58 (1H, m), 8.15-8.10 (4H, m), 8.05-8.08 (1H, m), 7.82-7.95 (3H, m), 7.55-7.60 (1H, m), 6.85 (2H, m), 3.45 (4H, m), 3.25 (2H, s), 2.72 (4H, m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. customThe solvent was evaporated in vacuo
  4. customthe crude reaction mixture
  5. customwas purified by preparative LCMS

Sources & evidence

ORD record
ord-a0fc12bdfc3440ac9486089975c2c738
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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