HCID 67016364, compound → HCID 67016220, compound

HRID 1918826Notes

Reaction equation

HRID 1918826 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C>[Si:1]([O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([NH2:16])[CH:13]=[N:12]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 67016364HCID 67016364, compound

Product 1

HCID 67016220HCID 67016220, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250-mL Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (50% wet, 150 mg dry weight) and a solution of 116a (1.11 g, 4.10 mmol) in ethanol (20 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 3 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (1.00 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a 100% yield of 116b (985 mg) as an orange oil: 1H NMR (500 MHz, CDCl3) d 7.18 (s, 1H), 7.11 (s, 1H), 4.09 (t, 2H, J=5.5 Hz), 3.89 (t, 2H, J=5.5 Hz), 3.25 (br s, 2H), 0.86 (s, 9H), −0.32 (s, 6H). MS (ESI+) m/z 242.2 (M+H).

Workup

  1. customA 250-mL Parr reactor bottle was purged with nitrogen
  2. additioncharged with 10% palladium on carbon (50% wet, 150 mg dry weight)
  3. customevacuated
  4. additioncharged with hydrogen gas to a pressure of 50 psi
  5. customAfter this time, the hydrogen was evacuated
  6. additionnitrogen was charged into the bottle
  7. additionCelite 521 (1.00 g) was added
  8. filtrationthe mixture was filtered through a pad of Celite 521
  9. washThe filter cake was washed with ethanol (2×25 mL)
  10. concentrationthe combined filtrates were concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7b2c2f606f29464aa7f6cc60832bad63
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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