HCID 178418361, compound → HCID 178508054, compound

HRID 1639627Notes

Reaction equation

HRID 1639627 reaction equation
[N:1]1([CH2:7][C:8]2[CH:24]=[CH:23][C:11]3[NH:12][C:13]([C:15]4[C:19]([N+:20]([O-])=O)=[CH:18][NH:17][N:16]=4)=[N:14][C:10]=3[CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>CN(C=O)C.[Pd]>[N:1]1([CH2:7][C:8]2[CH:24]=[CH:23][C:11]3[NH:12][C:13]([C:15]4[C:19]([NH2:20])=[CH:18][NH:17][N:16]=4)=[N:14][C:10]=3[CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178526864HCID 178526864, compound

Product 1

HCID 178508054HCID 178508054, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To 5-morpholin-4-ylmethyl-2-(4-nitro-1H-pyrazol-3-yl)1H-benzimidazole (1 mol. eq.) in DMF (36 vol.) under an atmosphere of nitrogen, was added 5% Pd/C (0.1 wt. eq.). The reaction vessel was charged with hydrogen and stirred at ambient temperature for 24 hours. The mixture was then filtered through celite, washing with methanol. The filtrate was concentrated in vacuo to give 3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine as a brown solid (90%). (LC/MS (basic method): Rt 1.94, [M−H+]− 297. The product was used without any further purification.

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ac7df214f5c04f9a91e5a172d4f1c57c
Source dataset
uspto-grants-2012_02
Patent number
US08110573B2

Reaction notes

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