Water → N-(10-methoxymethyl-10H-Pyrazino[2,3-b][1,4]benzothiazin-8-ylmethyl) chloro-acetamide
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:11][C:10]3[N:12]=[CH:13][CH:14]=[N:15][C:9]=3[N:8]([CH2:16][O:17][CH3:18])[C:7]=2[CH:19]=1.C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30].O>CN(C)C=O.ClCCl>[CH3:18][O:17][CH2:16][N:8]1[C:7]2[CH:19]=[C:3]([CH2:2][NH:1][C:29](=[O:30])[CH2:28][Cl:27])[CH:4]=[CH:5][C:6]=2[S:11][C:10]2[N:12]=[CH:13][CH:14]=[N:15][C:9]1=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
1.25 g of 8-aminomethyl-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine and 0.7 ml of triethylamine were dissolved in N,N-dimethylformamide (15 ml). Under ice-cooling, 2 ml of a solution of 0.4 ml of chloroacetyl chloride in dichloromethane was dropped thereinto and the resulting mixture was stirred for 1 hour. After adding water, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate). The crystals thus obtained were washed with n-hexane and thus 1.28 g of the title compound was obtained as a yellow powder.
Workup
- temperatureUnder ice-cooling
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
- concentrationAfter concentrating under reduced pressure
- customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)
- customThe crystals thus obtained
- washwere washed with n-hexane
Sources & evidence
- ORD record
- ord-f6608daa2c554987a8f6fd222c3cb18a
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518423B1
Reaction notes
Loading…