Sodium methanesulfinate → HCID 178457869, compound

HRID 518762Notes

Reaction equation

HRID 518762 reaction equation
Cl[C:2]1[CH:7]=[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)[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=1.[CH3:24][S:25]([O-:27])=[O:26].[Na+]>CN(C=O)C>[CH:18]([NH:17][C:15]([C@H:12]1[CH2:13][CH2:14][C@@H:9]([NH:8][C:6]2[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=[C:2]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:7]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 178457831HCID 178457831, compound

Product 1

HCID 178457869HCID 178457869, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (0.100 g, 0.293 mmol) in DMF (0.6 mL) was added sodium methanesulfinate (0.042 g, 0.352 mmol), and the reaction mixture was heated at 100° C. for 2 hours. The reaction was conducted twice and the mixtures were combined and concentrated under reduced pressure and the yellow residue purified by flash chromatography, eluting with 0-80% 9:1 DCM/MeOH:DCM to afford cis-N-isopropyl-4-(2-(methylsulfonyl)-5-nitropyridin-4-ylamino)cyclohexanecarboxamide as a yellow solid. MS (ESI pos. ion) m/z: 385.0 [M+H].

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe yellow residue purified by flash chromatography
  3. washeluting with 0-80% 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-f7bad36dd05a4282bfa5e3e74bd6c0d8
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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