HCID 21471655, compound → HCID 15839547, compound

HRID 2294926Notes

Reaction equation

HRID 2294926 reaction equation
[N:1]([C:4]1[N:9]=[C:8]([C:10]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:23][CH2:22][CH:21]([N:24]4[C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[NH:26][C:25]4=[O:33])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[O:11])[CH:7]=[N:6][CH:5]=1)=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[N:9]=[C:8]([C:10]([N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[CH2:19][CH2:20][CH:21]([N:24]4[C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[NH:26][C:25]4=[O:33])[CH2:22][CH2:23]3)[CH2:16][CH2:17]2)=[O:11])[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 2

HCID 21471655HCID 21471655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15839547HCID 15839547, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The crude 1,3-dihydro-1-{1-[1-(6-azido-2-pyrazinecarbonyl)piperidin-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one was hydrogenated under 1 atm. of hydrogen in 20 mL of ethanol over 0.05 g of 5% palladium on carbon. The catalyst was removed by filtration and the filtrate concentrated to dryness under reduced pressure. Preparative thin layer chromatography using 20% methanol/10% conc. NH4OH/70% chloroform gave 35 mg of 1,3-dihydro-1-{1-[1-(6-amino-2-pyrazinecarbonyl)piperidin-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one as a solid: 1H NMR (400 MHz, CDCl3) 8.12 (s, 1H), 8.02 (s, 1H), 7.85 (br s, 1H), 7.19-7.04 (m, 4H), 4.95 (br s, 1H), 4.62 (br s, 1H), 4.2 (br s, 1H), 3.65 (br s, 1H), 3.6-3.2 (m, 4H), 3.15 (m, 2H), 3.03 (m, 1H), 2.82 (m, 1H), 2.45-2.25 (m, 2H), 2.1-1.8 (m, 4H). The dihydrochloride salt was precipitated from chloroform/methanol: Analysis calculated for C21H27N7O2.0.45 CHCl3.0.65 NH4Cl: C: 46.25, H: 5.54, N: 18.38 found C: 46.28, H: 5.92, N: 18.48.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6d65f4ae6cd142a994105716f23ed95a
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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