Methyl iodide → (Z)-1,7-dimethyl-3-(2-methyl-5-(1-(methylthio)-3-oxo-3-(thiazol-2-yl)prop-1-enylamino)phenyl)-1,6-naphthyridin-2(1H)-one

HRID 2061189Notes

Reaction equation

HRID 2061189 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7].[H-].[Na+].[N:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:33])=[C:18]([C:20]2[C:21](=[O:32])[N:22]([CH3:31])[C:23]3[C:28]([CH:29]=2)=[CH:27][N:26]=[C:25]([CH3:30])[CH:24]=3)[CH:19]=1)=[C:12]=[S:13].[CH3:34]I>CN(C=O)C>[CH3:31][N:22]1[C:23]2[C:28](=[CH:27][N:26]=[C:25]([CH3:30])[CH:24]=2)[CH:29]=[C:20]([C:18]2[CH:19]=[C:14]([NH:11]/[C:12](/[S:13][CH3:34])=[CH:7]/[C:6](=[O:8])[C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[CH:15]=[CH:16][C:17]=2[CH3:33])[C:21]1=[O:32]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 5201082-AcetylthiazoleHCID 583690043-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

Product 1

HCID 58369005(Z)-1,7-dimethyl-3-(2-methyl-5-(1-(methylthio)-3-oxo-3-(thiazol-2-yl)prop-1-enylamino)phenyl)-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(thiazol-2-yl)ethanone (24.0 mg, 0.2 mmol) and NaH (16.0 mg, 0.4 mmol, 60% in mineral oil) in DMF (1 mL) was added 3-(5-isothiocyanato-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one 19 (64.5 mg, 0.2 mmol) at rt. The reaction was stirred for 1 h at rt. Then MeI (29 mg, 0.20 mmol) was added. The reaction was quenched with water after 10 min and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to yield crude (Z)-1,7-dimethyl-3-(2-methyl-5-(1-(methylthio)-3-oxo-3-(thiazol-2-yl)prop-1-enylamino)phenyl)-1,6-naphthyridin-2(1H)-one 32 which was used without purification. MS m/z 463.1 (M+1).

Workup

  1. customThe reaction was quenched with water after 10 min
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a668f9c56154d969708a85f987a8814
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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