HCID 178526861, compound → HCID 178508050, compound

HRID 660155Notes

Reaction equation

HRID 660155 reaction equation
[N+:1]([C:4]1[C:5]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[N:6][NH:7][CH:8]=1)([O-])=O>CO>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:5]2[C:4]([NH2:1])=[CH:8][NH:7][N:6]=2)[CH:10]=1

Participants

3

Reactant 1

HCID 178526861HCID 178526861, compound

Product 1

HCID 178508050HCID 178508050, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 38 (0.37 g, 1.9 mmol) was dissolved in MeOH (containing Pd(OH)2/C (0.03 g)). Hydrogenation was accomplished within 3 hours (1 atm) at room temperature. The reaction mixture was filtered, washed with ethyl acetate/MeOH (1/1) and concentrated in vacuo. The resulting residue was purified by flash chromatography (ethyl acetate followed by ethyl acetate/MeOH 1/1) to afford compound 39 as an oil (0.29 g, 95%). 1H-NMR (200 MHz, CDCl3 and D6DMSO 1/1): δ 9.05 (d, J=2 Hz, 1H), 8.51 (d, J=5 Hz, 2 Hz, 1H), 8.09 (dt, J=8 Hz, 2 Hz, 1H), 7.43 (s, 1H), 7.37-7.32 (m, 1H).

Workup

  1. customat room temperature
  2. filtrationThe reaction mixture was filtered
  3. washwashed with ethyl acetate/MeOH (1/1)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (ethyl acetate followed by ethyl acetate/MeOH 1/1)

Sources & evidence

ORD record
ord-35e5e6027c5e455886ba09de0230227e
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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