HCID 178418361, compound → HCID 178508054, compound

HRID 1622420Notes

Reaction equation

HRID 1622420 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-83c76554fd14452cb89d019aa95e23fa
Source dataset
uspto-grants-2014_07
Patent number
US08778936B2

Reaction notes

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