2,6-Lutidine → HCID 86691230, compound

HRID 1483023Notes

Reaction equation

HRID 1483023 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]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 12164755(S)-1-(4-Bromophenyl)-2,2,2-trifluoroethanamine

Product 1

HCID 86691230HCID 86691230, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

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 the mixture at that temperature for 20 h. Dilute the reaction mixture with DCM (300 mL) and wash it sequentially with aqueous HCl (2 M, 2×200 mL), water (250 mL), then brine (250 mL). Collect the organic phase; dry over MgSO4; 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

  1. washwash it sequentially with aqueous HCl (2 M, 2×200 mL), water (250 mL)
  2. customCollect the organic phase
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationand concentrate the filtrate under reduced pressure
  6. customTriturate the residue with hexane (200 mL) for 10 minutes
  7. filtrationfilter
  8. customand dry the solid under reduced pressure

Sources & evidence

ORD record
ord-7b6b9cc571c74a9c837e481e3c6a606b
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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