Reaction equation
[Br:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([N:15]2[CH2:20][CH2:19][N:18](S(CC)(=O)=O)[CH2:17][CH2:16]2)=[N:4][C:3]=1[C:26]1[CH:27]=[C:28]([O:33][CH3:34])[C:29]([NH2:32])=[N:30][CH:31]=1>C1COCC1.CN(C=O)C>[Br:1][C:2]1[N:6]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([N:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)=[N:4][C:3]=1[C:26]1[CH:27]=[C:28]([O:33][CH3:34])[C:29]([NH2:32])=[N:30][CH:31]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Preparation of 5-(5-bromo-2-(4-(ethylsulfonyl)piperazin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-3-methoxypyridin-2-amine: In a 10 mL round-bottomed flask was 5-(5-bromo-2-(piperazin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)-3-methoxypyridin-2-amine (22 mg, 0.046 mmol) in THF (1.2 ml) and DMF (0.2 mL) under Ar at 0° C. to give a colorless solution. Ethanesulfonyl chloride (8.62 μl, 0.091 mmol) and triethylamine (0.014 ml, 0.100 mmol) were added. The ice bath was removed and the mixture was stirred at ambient temperature for 30 min. The mixture was quenched with water (3 mL) and diluted with EtOAc (10 mL). The aq layer was extracted with EtOAc (2×10 mL). The combined org layers were washed with sat aq NaHCO3 solution (1×30 mL), brine (1×30 mL), dried over Na2SO4, filtered and conc in vacuo. The crude material was directly used in the next step without purification: LCMS (m/z): 577.2 (MH+), tR=0.82 min.
Workup
- customIn a 10 mL round-bottomed flask was
Sources & evidence
- ORD record
- ord-e09eabb1bddf4950ac922d22aaf0769d
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129394B2
Linked notes
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