Methanesulfonyl chloride → HCID 178473725, compound
Reaction equation
CS([Cl:5])(=O)=O.Cl.Cl.Cl.[NH:9]1[CH:13]=[C:12]([CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][C:24]([C:26]4[CH:27]=N[CH:29]=[CH:30][CH:31]=4)=[CH:25][C:20]=3[CH2:19][N:18]([C:32](=[O:37])[C:33](F)(F)F)[CH:17]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:16]2)[N:11]=[CH:10]1.[CH3:45]CN(C(C)C)C(C)C>C(Cl)Cl>[ClH:5].[C:32]([N:18]1[CH2:19][C:20]2[CH:25]=[C:24]([C:26]3[CH:27]=[CH:45][CH:29]=[CH:30][CH:31]=3)[CH:23]=[CH:22][C:21]=2[N:15]([CH2:14][C:12]2[N:11]=[CH:10][NH:9][CH:13]=2)[CH2:16][C@H:17]1[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)(=[O:37])[CH3:33]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Methylsulfonylchloride (0.031 ml, 0.39 mmol) was added dropwise to a solution of Compound B (0.070 g, 0.27 mmol) and DIEA (0.14 ml, 0.80 mmol) in methylene chloride (2 ml) at -78° C. The mixture was allowed to warm slowly to room temperature and was stirred at rt for 16h. The mixture was quenched with 10% NaHCO3 (10 ml) and the solution was extracted with methylene chloride (3×10 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by flash chromatography (19/1 methylene chloride/iPrOH) to afford Compound C (0.064 g, 85%) as a solid. MS (M+H)+ 343
Workup
- customThe mixture was quenched with 10% NaHCO3 (10 ml)
- extractionthe solution was extracted with methylene chloride (3×10 ml)
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe residue was purified by flash chromatography (19/1 methylene chloride/iPrOH)
Sources & evidence
- ORD record
- ord-d139a4d81812473bbfe24e56a8c45baa
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06011029
Reaction notes
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