Sodium Methoxide → HCID 16118692, compound

HRID 1787607Notes

Reaction equation

HRID 1787607 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:13]3[S:14][CH:15]=[C:16]([CH3:18])[N:17]=3)[N:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:19][O-:20].[Na+]>S1(CCCC1)(=O)=O.O>[CH3:19][O:20][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][C:13]3[S:14][CH:15]=[C:16]([CH3:18])[N:17]=3)[N:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 16118690HCID 16118690, compound

Product 1

HCID 16118692HCID 16118692, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (2-chloro-[1,7]naphthyridin-8-yl)-(4-methyl-thiazol-2-yl)-amine (0.055 g, 0.20 mmol) in 1.5 ml sulfolane was added g sodium methylate (0.55, 1.0 mmol). The reaction mixture was heated for 10 min at 100° C. under microwave irradiation. The reaction mixture was diluted with water and extracted with three portions of methyl-tert.-butyl ether. The combined organic layers were washed with two portions of water, dried over sodium sulfate and concentrated to dryness. Flash-chromatography gave the title compound (0.043 g, 79%) as an off-white solid, MS m/e (%): 273 (M+H+, 100).

Workup

  1. extractionextracted with three portions of methyl-tert.-butyl ether
  2. washThe combined organic layers were washed with two portions of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-450e80bcc42c4eca88a27fa08fd2eb33
Source dataset
uspto-grants-2009_03
Patent number
US07511055B2

Reaction notes

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