HCID 86683761, compound → HCID 86683762, compound

HRID 519379Notes

Reaction equation

HRID 519379 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 125a (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 Celite and the filtrate was concentrated under reduced pressure to afford 125b (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 Celite
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8004891673dc49ba8c2571015178ad4a
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

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