Sodium Iodide → HCID 67098449, compound

HRID 2076809Notes

Reaction equation

HRID 2076809 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:7]1=[O:14].[CH3:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[N:17]=1.C(N(CC)CC)C.[I-].[Na+]>CN(C)C=O>[ClH:1].[CH3:13][O:12][C:8]1[C:7](=[O:14])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:29]2[CH2:30][CH2:31][N:26]([C:22]3[CH:21]=[CH:20][CH:19]=[C:18]4[C:23]=3[CH:24]=[CH:25][C:16]([CH3:15])=[N:17]4)[CH2:27][CH2:28]2)[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 498519012-Methyl-5-piperazin-1-yl-quinolineHCID 592346471-(4-Chlorobutyl)-3-methoxy-1H-pyridin-2-one

Product 1

HCID 67098449HCID 67098449, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-chlorobutyl)-3-(methyloxy)-2(1H)-pyridinone (67.8 mg, 0.31 mmol), 2-methyl-5-(1-piperazinyl)quinoline (see WO2004/046124 D3) (77.5 mg, 0.34 mmol), triethylamine (0.09 mL, 0.64 mmol) and a catalytic amount of sodium iodide in anhydrous N,N-dimethylformamide (2.50 mL) was stirred at 110° C. overnight. The reaction mixture was concentrated in vacuo, taken-up in dichloromethane (5 mL) and washed with water (2×5 mL). The organic layer was dried (Na2SO4) and evaporated in vacuo. The crude product was passed through a SCX cartridge, washing with methanol and eluting with ammonia 2M in methanol and then purified by flash chromatography on silica gel, eluting with 2% methanol in dichloromethane, to afford the corresponding free base of the title compound as a yellow solid (65.9 mg, 52%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo, taken-up in dichloromethane (5 mL)
  2. washwashed with water (2×5 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated in vacuo
  5. washwashing with methanol
  6. washeluting with ammonia 2M in methanol
  7. custompurified by flash chromatography on silica gel
  8. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-2f448596b08345dbb4dac376ad8220a1
Source dataset
uspto-grants-2011_04
Patent number
US07928108B2

Reaction notes

Loading…