2,6-Lutidine → HCID 86691230, compound
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([NH2:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1.N1C(C)=CC=CC=1C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([NH:18][S:2]([CH3:1])(=[O:4])=[O:3])[C:14]([F:16])([F:17])[F:15])=[CH:9][CH:8]=1Participants
Procedure
Add methanesulfonyl chloride (16.42 mL, 0.21 mol) drop-wise to a mixture of (1S)-1-(4-bromophenyl)-2,2,2-trifluoroethanamine (49 g, 0.19 mol), 4-dimethylaminopyridine (1.18 g, 9.0 mmol), 2,6-lutidine (67 mL, 0.57 mol) in DCM (250 mL) at 0° C. Warm the mixture to ambient temperature and stir at that temperature for 20 hours. Dilute the reaction mixture with DCM (300 mL) and wash it sequentially with 2M HCl (2×200 mL), water (250 mL), then brine (250 mL). Collect the organic phase and dry over magnesium sulphate; filter; and concentrate the filtrate under reduced pressure. Triturate the residue with hexane (200 mL) for 10 minutes; filter; and dry the solid under reduced pressure to provide the title compound as a pale brown solid (60 g, 93% yield, 98% ee). MS (m/z): 332 (M+1).
Workup
- washwash it sequentially with 2M HCl (2×200 mL), water (250 mL)
- customCollect the organic phase
- dry with materialdry over magnesium sulphate
- filtrationfilter
- concentrationand concentrate the filtrate under reduced pressure
- customTriturate the residue with hexane (200 mL) for 10 minutes
- filtrationfilter
- customand dry the solid under reduced pressure
Sources & evidence
- ORD record
- ord-17c3a081562446138cdac56e6f11052f
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575352B2
Reaction notes
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