HCID 21875489, compound → HCID 21875359, compound

HRID 723679Notes

Reaction equation

HRID 723679 reaction equation
[N+:1]([C:4]1[C:13]2[N:12]=[CH:11][CH:10]=[N:9][C:8]=2[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:1][C:4]1[C:13]2[NH:12][CH2:11][CH2:10][NH:9][C:8]=2[C:7]([C:14]#[N:15])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 21875489HCID 21875489, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21875359HCID 21875359, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 468A (0.037 g, 0.18 mmol) was dissolved in a mixture of ethyl acetate (1.0 mL)/ethanol (1.0 mL) and 10% Pd/C (0.050 g) was added. Hydrogen was then introduced via a balloon. After 2 h, the reaction was purged with nitrogen and filtered through Celite, rinsing with ethyl acetate. Concentration in vacuo gave 0.029 g (90%) of compound 469A as a red oil, which was taken on without further purification. HPLC: 97% at 3.217 min (retention time) (YMC S5 ODS column, 4.6×50 mm, eluting with 10–90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. additionwas added
  2. customthe reaction was purged with nitrogen
  3. filtrationfiltered through Celite
  4. washrinsing with ethyl acetate
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c4f6adbee6e64617b02899c782118138
Source dataset
uspto-grants-2006_11
Patent number
US07141578B2

Reaction notes

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