Water → HCID 67278062, compound

HRID 1696250Notes

Reaction equation

HRID 1696250 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([N:16]3[C:20]4=[C:21]5[CH:27]=[CH:26][NH:25][C:22]5=[N:23][CH:24]=[C:19]4[NH:18][C:17]3=[O:28])[CH2:11]2)=[N:8][CH:9]=1)([O-])=O.O.C([O-])=O.[NH4+]>C(O)C.O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][CH2:13][C@@H:12]([N:16]3[C:20]4=[C:21]5[CH:27]=[CH:26][NH:25][C:22]5=[N:23][CH:24]=[C:19]4[NH:18][C:17]3=[O:28])[CH2:11]2)=[N:8][CH:9]=1

Participants

7

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 57916228HCID 57916228, compound

Product 1

HCID 67278062HCID 67278062, compoundYield 47.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-[(3R)-1-(5-nitro-2-pyridinyl)-3-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (19.3 mg) in ethanol (3 mL), tetrahydrofuran (1 mL), and water (0.15 mL) was added 10% Pd—C (50% wet, 10 mg) and ammonium formate (32 mg). After stirring for 50 minutes at 75° C., catalyst was removed by filtration, and solvent was also removed under reduced pressure. The residue was dissolved in EtOAc, washed with saturated aqueous sodium hydrogencarbonate, and brine, dried over MgSO4, evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1 to 8:1) to give 1-[(3R)-1-(5-amino-2-pyridinyl)-3-piperidinyl]-3,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-2(1H)-one (8.5 mg) as a pale brown crystals.

Workup

  1. customcatalyst was removed by filtration, and solvent
  2. customwas also removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated aqueous sodium hydrogencarbonate, and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:1 to 8:1)

Sources & evidence

ORD record
ord-897af8ff1d8e44038c33c8f73b5f07c0
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

Loading…