HCID 86683761, compound → HCID 86683762, compound

HRID 592792Notes

Reaction equation

HRID 592792 reaction equation
[CH3:1][C:2]1([CH3:24])[N:7]([C:8]2[CH:9]=[N:10][C:11]([N+:14]([O-])=O)=[CH:12][CH:13]=2)[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1>[Pd].CO>[NH2:14][C:11]1[N:10]=[CH:9][C:8]([N:7]2[CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3][C:2]2([CH3:24])[CH3:1])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 86683761HCID 86683761, compound

Product 1

HCID 86683762HCID 86683762, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 50-mL round-bottomed flask was purged with nitrogen and charged with tert-butyl 3,3-dimethyl-4-(6-nitropyridin-3-yl)piperazine-1-carboxylate 190a (1100 mg, 3.2 mmol), 10% palladium on carbon (10% wet, 110 mg), and methanol (20 mL). It was then evacuated, charged with hydrogen gas, and stirred at room temperature for 5 h. The hydrogen was evacuated and nitrogen was charged into the flask. The catalyst was removed by filtration through a pad of diatomaceous earth filter agent (CELITE®, Imerys Minerals California, Inc.) and the filtrate was concentrated under reduced pressure to afford 190b (950 mg, 94%). LCMS: [M+H]+ 307.3

Workup

  1. customA 50-mL round-bottomed flask was purged with nitrogen
  2. customIt was then evacuated
  3. additioncharged with hydrogen gas
  4. customThe hydrogen was evacuated
  5. additionnitrogen was charged into the flask
  6. customThe catalyst was removed by filtration through a pad of diatomaceous earth
  7. filtrationfilter agent (CELITE®, Imerys Minerals California, Inc.)
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4d979fa63a0d47e1a3cb2dc50d0dd28b
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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