Dichloromethane → HCID 178457868, compound

HRID 518763Notes

Reaction equation

HRID 518763 reaction equation
[CH:1]([NH:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][N:17]=[C:16]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[Sn](Cl)Cl.C(Cl)Cl>CO>[NH2:20][C:19]1[C:14]([NH:13][C@@H:10]2[CH2:9][CH2:8][C@H:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:12][CH2:11]2)=[CH:15][C:16]([S:23]([CH3:26])(=[O:24])=[O:25])=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24479Stannous ChlorideHCID 178457869HCID 178457869, compound

Product 1

HCID 178457868HCID 178457868, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of cis-N-isopropyl-4-(2-(methylsulfonyl)-5-nitropyridin-4-ylamino)cyclohexanecarboxamide (0.177 g, 0.460 mmol) in MeOH (2 mL) was added anhydrous tin (II) chloride (0.349 g, 1.842 mmol). The reaction mixture was heated at 80° C. for 3 hours and was concentrated under vacuum. The remaining residue was dissolved in EtOAc and washed with 1N aqueous NaOH followed by brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 0-100% 90/10/1 DCM/MeOH/NH4OH:DCM to afford cis-4-(5-amino-2-(methylsulfonyl)pyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (0.150 g, 92% yield). MS (ESI pos. ion) m/z: 355.2 [M+H].

Workup

  1. concentrationwas concentrated under vacuum
  2. dissolutionThe remaining residue was dissolved in EtOAc
  3. washwashed with 1N aqueous NaOH
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography
  7. washeluting with 0-100% 90/10/1 DCM/MeOH/NH4OH

Sources & evidence

ORD record
ord-3345b17920c8485aa695cdcff26e566e
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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