HCID 58564655, compound → HCID 58564607, compound

HRID 2039970Notes

Reaction equation

HRID 2039970 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[NH:20][C:12]3=[N:13][CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=[C:11]3[CH:10]=2)=[O:8])[CH2:3][CH2:2]1.[H][H]>[Pd].CO>[NH2:17][C:15]1[CH:16]=[C:11]2[CH:10]=[C:9]([C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[O:8])[NH:20][C:12]2=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 58564655HCID 58564655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58564607HCID 58564607, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

An autoclave is charged with 313 mg (1.13 mmol) of the morpholino(5-nitro-1H-pyrrolo[2,3-b]pyridin-2-yl)methanone formed during the preceding stage, 100 mL of methanol and 31 mg of palladium on charcoal at 10%. The autoclave is placed under 20 bar of hydrogen and the solution is stirred at room temperature for 18 hours, The solution is then filtered on Celite, the Celite is rinsed with 50 mL of methanol and the filtrate is evaporated under reduced pressure. 280 mg of a white solid is recovered, and is used in the next stage without further purification (quantitative raw yield).

Workup

  1. filtrationThe solution is then filtered on Celite
  2. washthe Celite is rinsed with 50 mL of methanol
  3. customthe filtrate is evaporated under reduced pressure
  4. custom280 mg of a white solid is recovered
  5. customis used in the next stage without further purification (quantitative raw yield)

Sources & evidence

ORD record
ord-8b6ad2de609d41178f7eea23523bc361
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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