3-Nitro-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridin-6-yl acetate → 6-acetoxy-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridin-3-amine

HRID 1967467Notes

Reaction equation

HRID 1967467 reaction equation
[C:1]([O:4][CH:5]1[C:9]2=[N:10][C:11]3[C:12](=[N:13][CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=3)[N:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:4][CH:5]1[C:9]2=[N:10][C:11]3[C:12](=[N:13][CH:14]=[C:15]([NH2:17])[CH:16]=3)[N:8]2[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 669051873-Nitro-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridin-6-yl acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 594026426-acetoxy-7,8-dihydro-6H-pyrrolo[2',1':2,3]imidazo[4,5-b]pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 0.25 g (0.95 mmol) of 3-nitro-7,8-dihydro-6H-pyrrolo[2′,1′:2,3]imidazo[4,5-b]pyridin-6-yl acetate, obtained in the preceding step, and 0.21 g of 10% palladium on carbon in 60 ml of ethanol is stirred at 20° C. for 3 hours under five atmospheres of hydrogen. After this time the mixture is filtered on a bed of celite and then concentrated under reduced pressure. This gives 0.22 g of the expected product, which will be used as it is in the remainder of the synthesis.

Workup

  1. filtrationAfter this time the mixture is filtered on a bed of celite
  2. concentrationconcentrated under reduced pressure
  3. customis in the remainder of the synthesis

Sources & evidence

ORD record
ord-74cd775ec0e4402c9140d521799f3766
Source dataset
uspto-grants-2013_04
Patent number
US08420817B2

Reaction notes

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