HCID 123928403, compound → HCID 123244203, compound

HRID 1509228Notes

Reaction equation

HRID 1509228 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][C:21]([N+:30]([O-])=O)=[C:20]([CH2:33][N+:34]([O-])=O)[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CCO.[Ni]>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][C:21]([NH2:30])=[C:20]([CH2:33][NH2:34])[N:19]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 123928403HCID 123928403, compound

Product 1

HCID 123244203HCID 123244203, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of tert-butyl(1-(4-(5-nitro-6-(nitromethyl)-3-phenylpyridin-2-yl)phenyl)cyclobutyl)carbamate (74 mg, 0.15 mmol) in EtOH (50 mL) was added Raney Nickel (17 mg, 0.15 mmol). The resulting mixture was purged with nitrogen and with H2 and then stirred under H2 (1.5 bars) overnight at room temperature. The black mixture was filtered through celite, rinsed few times with EtOH (making sure that the cake remained wet at all times), dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was used directly without purification.

Workup

  1. customThe resulting mixture was purged with nitrogen and with H2
  2. filtrationThe black mixture was filtered through celite
  3. washrinsed few times with EtOH (
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resulting residue was used directly without purification

Sources & evidence

ORD record
ord-b52d5dc8d80d4325a0faa179d6019f44
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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