Sodium methanesulfinate → HCID 178457867, compound

HRID 518768Notes

Reaction equation

HRID 518768 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:7]=1.[CH3:24][S:25]([O-:27])=[O:26].[Na+]>CN(C=O)C.C(Cl)Cl.CO>[CH:18]([NH:17][C:15]([C@H:12]1[CH2:13][CH2:14][C@@H:9]([NH:8][C:6]2[CH:7]=[C:2]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:3]=[CH:4][C:5]=2[N+:21]([O-:23])=[O:22])[CH2:10][CH2:11]1)=[O:16])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 178457839HCID 178457839, compound

Product 1

HCID 178457867HCID 178457867, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of cis-4-(5-fluoro-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (0.100 g, 0.309 mmol) in DMF (0.55 mL) was added sodium methanesulfinate (0.045 g, 0.371 mmol), and the reaction mixture was heated at 100° C. for 2 hours. The mixture was concentrated under vacuum, and the residue was purified by flash chromatography, eluting with 0-70% 9:1 DCM/MeOH to cis-N-isopropyl-4-(5-(methylsulfonyl)-2-nitrophenylamino)cyclohexanecarboxamide as a bright orange solid (0.124 g, 105% yield). MS (ESI pos. ion) m/z: 384.0 [M+H].

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5a5bb5ed5e58428a8655939198a3b983
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…