Methyl iodide → HCID 21948137, compound

HRID 2183783Notes

Reaction equation

HRID 2183783 reaction equation
CI.[C:3]([O-])([O-])=O.[K+].[K+].[NH:9]([C:16]1[N:17]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:18]2[C:23]([C:24](=[O:26])[CH:25]=1)=[C:22]([CH3:27])[CH:21]=[C:20]([Cl:28])[N:19]=2)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Cl:28][C:20]1[N:19]=[C:18]2[C:23]([C:24](=[O:26])[CH:25]=[C:16]([N:9]([CH3:3])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:17]2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:22]([CH3:27])[CH:21]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21948152HCID 21948152, compound

Product 1

HCID 21948137HCID 21948137, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

MeI (0.10 mL, 228 mg, 1.6 mmol) was added to a stirred suspension of K2CO3 (23.5 mg, 0.17 mmol) and 2-anilino-7-chloro-5-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (50 mg, 0.14 mmol) in THF (3 mL). The suspension was heated to 40° C. and stirred was overnight. The reaction was quenched with water (5.0 mL) and extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. Recrystallization of the residue using EtOAc afforded 7-chloro-5-methyl-2-[methyl(phenyl)amino]-1-phenyl-1,8-naphthyridin-4(1H)-one (18 mg, 35%): LCMS RT: 2.24 min, MH+: 376.6, Rf=0.76 (4:1 Hex:EtOAc).

Workup

  1. customThe reaction was quenched with water (5.0 mL)
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customRecrystallization of the residue

Sources & evidence

ORD record
ord-99f302f0d11e4fd9ba29763664b47b66
Source dataset
uspto-grants-2005_05
Patent number
US06900205B2

Reaction notes

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