Methyl iodide → HCID 22397218, compound

HRID 411205Notes

Reaction equation

HRID 411205 reaction equation
IC.[Cl:3][C:4]1[CH:25]=[CH:24][C:7]([CH2:8][NH:9][C:10]([C:12]2[C:13](=[O:23])[C:14]3[CH:21]=[C:20]([I:22])[CH:19]=[N:18][C:15]=3[NH:16][N:17]=2)=[O:11])=[CH:6][CH:5]=1.[CH2:26](N(CC)CC)C>C(#N)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]([C:12]2[C:13](=[O:23])[C:14]3[CH:21]=[C:20]([I:22])[CH:19]=[N:18][C:15]=3[N:16]([CH3:26])[N:17]=2)=[O:11])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 22397155HCID 22397155, compound

Product 1

HCID 22397218HCID 22397218, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodomethane (0.6 mL) is added to a mixture of N-(4-chlorobenzyl)-6-iodo-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxamide (Preparation 22, 0.196 g) and triethyl-amine (70 μL) in acetonitrile (10 mL) and the mixture is stirred at room temperature for 48 h. The reaction mixture is concentrated, and the residue is dissolved in chloroform and water. The organic phase is dried (Na2SO4) and concentrated in vacuo. The crude product is purified by flash chromatography on silica gel (240-400 mesh, 7 g) eluting with 2% methanol/chloroform. The product fractions are pooled and concentrated in vacuo to give 0.16 g of the title compound as a yellow solid. Physical characteristics: mp 207-208° C.; 1H NMR (400 MHz, CDCl3) δ 4.39, 4.70, 7.33, 9.0, 9.1, 10.0; IR (drift) 1676, 1608, 1574, 1550, 1493, 1470, 1397, 1393, 1370, 1320, 1267, 1257, 812, 673, 666 cm−1; MS (EI) m/z 454 (M+, 61); HRMS (FAB) m/z 454.9767 (C16H12ClIN4O2+H). Anal. Found: C, 42.10; H, 2.61; N, 12.22.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionthe residue is dissolved in chloroform
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography on silica gel (240-400 mesh, 7 g)
  6. washeluting with 2% methanol/chloroform
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e71fdf32b5d54d5e841b83e16dc600b8
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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