Chlorotrimethylsilane → HCID 58513618, compound
Reaction equation
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33].Cl[Si](C)(C)C>CO>[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][C:12]([S:14]([CH2:17][CH:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)(=[O:16])=[O:15])=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:31][C:32]([CH3:34])([CH3:33])[CH3:35]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of tert-butyl 4-((1-(2-(dimethylamino)ethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)methyl)piperidine-1-carboxylate (STEP B, 1.48 g, 2.84 mmol) and chlorotrimethylsilane (1.45 mL, 11.4 mmol) in methanol (5 mL) was stirred at 50° C. for 1.5 h. The reaction mixture was concentrated in vacuo, followed by addition of dichloromethane (100 ml). The resulting mixture was washed with sodium bicarbonate aqueous solution and brine and dried over sodium sulfate. The resulting solution was concentrated and the residue was purified by silica gel column chromatography (pre-treatment with triethylamine, dichloromethane-ethyl acetate=100:0 to 0:100) to give the title compound (1.18 g, 84%).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- additionfollowed by addition of dichloromethane (100 ml)
- washThe resulting mixture was washed with sodium bicarbonate aqueous solution and brine
- dry with materialdried over sodium sulfate
- concentrationThe resulting solution was concentrated
- customthe residue was purified by silica gel column chromatography (pre-treatment with triethylamine, dichloromethane-ethyl acetate=100:0 to 0:100)
Sources & evidence
- ORD record
- ord-6dfbb5167f1148969f2a6ce4ebdaebd6
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653063B2
Reaction notes
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