N-Methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide → 8-[(6-Bromopyridin-2-yl)-(tert-butyldimethylsiloxy)methyl]-10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazine
Reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9]2[CH:10]=[C:11]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[N:17]=3)[OH:15])[CH:12]=[CH:13][C:8]=2[S:7][C:6]2[N:23]=[CH:24][CH:25]=[N:26][C:5]1=2.[Si:27](N(C)C(=O)C(F)(F)F)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]>C(#N)C>[Br:22][C:18]1[N:17]=[C:16]([CH:14]([O:15][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C:11]2[CH:12]=[CH:13][C:8]3[S:7][C:6]4[N:23]=[CH:24][CH:25]=[N:26][C:5]=4[N:4]([CH2:3][O:2][CH3:1])[C:9]=3[CH:10]=2)[CH:21]=[CH:20][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1.05 g of (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)-(6-bromopyridin-2-yl)methanol in 15 ml of acetonitrile was added in a nitrogen atmosphere 3.2 ml of N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide and the resulting mixture was stirred at room temperature for 22 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.72 g of the title compound as a yellow solid.
Workup
- distillationAfter distilling off the solvent under reduced pressure
- customthe residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-0091e12ccb3b4185af6a99042e3d732b
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518423B1
Reaction notes
Loading…