Dichloromethane → HCID 178457866, compound

HRID 518769Notes

Reaction equation

HRID 518769 reaction equation
[CH:1]([NH:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[CH:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=2[N+:24]([O-])=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C([O-])=O.[NH4+].C(Cl)Cl>CO.[Pd]>[NH2:24][C:15]1[CH:16]=[CH:17][C:18]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:19][C:14]=1[NH:13][C@@H:10]1[CH2:9][CH2:8][C@H:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 2723923Ammonium formateHCID 178457867HCID 178457867, compound

Product 1

HCID 178457866HCID 178457866, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of cis-N-Isopropyl-4-(5-(methylsulfonyl)-2-nitrophenylamino)cyclohexanecarboxamide (0.120 g, 0.313 mmol) in MeOH (1.2 mL) was added 5% Pd/C (0.067 g, 0.031 mmol) and ammonium formate (0.154 mL, 3.13 mmol) (exotherm). The reaction mixture was stirred at 20° C. for 1 hour and then the mixture was filtered through a pad of Celite® brand filter aid, washing with MeOH. The filtrate was concentrated under vacuum, and the remaining residue was dissolved in DCM then washed with water. The organic layer was concentrated under vacuum. The residue was purified by flash chromatography, eluting with 0-80% 90:10:1 DCM/MeOH/NH4OH:DCM to afford cis-4-(2-amino-5-(methylsulfonyl) phenylamino)-N-isopropylcyclohexanecarboxamide as a pale yellow oil (0.107 g, 97% yield). MS (ESI pos. ion) m/z: 354.2 [M+H].

Workup

  1. filtrationthe mixture was filtered through a pad of Celite® brand
  2. filtrationfilter aid
  3. washwashing with MeOH
  4. concentrationThe filtrate was concentrated under vacuum
  5. dissolutionthe remaining residue was dissolved in DCM
  6. washthen washed with water
  7. concentrationThe organic layer was concentrated under vacuum
  8. customThe residue was purified by flash chromatography
  9. washeluting with 0-80% 90:10:1 DCM/MeOH/NH4OH

Sources & evidence

ORD record
ord-7b2ce9c5a9bf49ebac695dbfae3a358f
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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