Methyl iodide → 6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-3-isopropyl-1-methyl-4-(methylamino)-1,8-naphthyridin-2(1H)-one

HRID 13845Notes

Reaction equation

HRID 13845 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:10]=2)[N:5]([CH3:27])[C:4](=[O:28])[C:3]=1[CH:29]([CH3:31])[CH3:30].[H-].[Na+].I[CH3:35]>C1COCC1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:9]2[CH:10]=[C:11]3[C:6](=[N:7][C:8]=2[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[N:5]([CH3:27])[C:4](=[O:28])[C:3]([CH:29]([CH3:31])[CH3:30])=[C:2]3[NH:1][CH3:35])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 114769994-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-3-isopropyl-1-methyl-1,8-naphthyridin-2(1H)-one

Product 1

HCID 113976296-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-3-isopropyl-1-methyl-4-(methylamino)-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of EXAMPLE 54 (30 mg) in THF (2.5 mL) was combined with sodium hydride (5 mg, 60% in mineral oil). The suspension was stirred for 10 min were upon iodomethane (37 uL) was added. The reaction was stirred for about 6.5 hours at room temperature. The reaction mixture was quenched with saturated aqueous NaHCO3 and diluted with EtOAc. The EtOAc solution was dried (Na2SO4). The concentrated residue was purified by preparative TLC on silica gel eluted with 35% EtOAc in hexane affording the title compound. HPLC/MS: 486.2 (M+1), 488.2 (M+3); Rt=4.72 min.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred for about 6.5 hours at room temperature
  3. customThe reaction mixture was quenched with saturated aqueous NaHCO3
  4. additiondiluted with EtOAc
  5. dry with materialThe EtOAc solution was dried (Na2SO4)
  6. customThe concentrated residue was purified by preparative TLC on silica gel
  7. washeluted with 35% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-2bc9788879ba4578941daef6db23936a
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Reaction notes

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