HCID 12388130, compound → HCID 23393898, compound

HRID 909952Notes

Reaction equation

HRID 909952 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)([O-])=O>CO>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 12388130HCID 12388130, compound

Product 1

HCID 23393898HCID 23393898, compoundYield 98,348.398%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 8 (0.73 g/0.0027 mmol) was then dissolved in 20 ml absolute methanol/2 ml THF and placed in a 500 ml Parr bottle. The bottle was flushed with nitrogen gas and then ˜200 mg 5% Pd—C added as catalyst. The resultant mixture was hydrogenated in a Parr Hydrogenator for 1 hour at ˜40 psi hydrogen. The initial uptake of hydrogen was rapid. The excess catalyst was removed by suction filtration through Celite, the filter cake washed with methanol and the filtrate evaporated in vacuo. The product crystallizes to afford 0.63 g of an off-white solid (97% yield). This compound was used without further purification. 1H NMR (d6-DMSO): δ 6.9 (d, J=4.4 Hz, 2H), 6.49 (d, J=4.4 Hz, 2H), 5.02 (s, 2H, —NH2), 3.81 (dd, J=11 Hz, 6 Hz, 1H), 3.56 (s, 3H), 3.55 (s, 3H), 2.99 (dd, J=11 Hz, 17 Hz, 1H), 2.59 (dd, J=17 Hz, 6 Hz, 1H). NP-TLC (CH2Cl2): Rf˜0.1; NP-TLC (1% CH3OH in CH2Cl2): Rf˜0.6; RP-TLC (1:1 CH3OH—H2O): Rf˜0.5.

Workup

  1. customThe bottle was flushed with nitrogen gas
  2. addition˜200 mg 5% Pd—C added as catalyst
  3. customThe excess catalyst was removed by suction filtration through Celite
  4. washthe filter cake washed with methanol
  5. customthe filtrate evaporated in vacuo
  6. customThe product crystallizes

Sources & evidence

ORD record
ord-8e88f68d8d264f89b91495f76af439e1
Source dataset
uspto-grants-2011_09
Patent number
US08021471B2

Reaction notes

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