HCID 178526864, compound → HCID 178508054, compound

HRID 1012140Notes

Reaction equation

HRID 1012140 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>[Pd].CN(C=O)C>[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

4

Reactant 1

HCID 178526864HCID 178526864, compound

Product 1

HCID 178508054HCID 178508054, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium on carbon (10%, 0.08 g) was added to solution of 5-morpholin-4-ylmethyl-2-(4-nitro-1H-pyrazol-3-yl)1H-benzimidazole (0.82 g, 2.5 mmol) in DMF (30 ml) under an atmosphere of nitrogen. The mixture was shaken under a hydrogen atmosphere for 4 h 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 (530 mg, 71%). (LC/MS: Rt 1.94, [M+H]+ 299).

Workup

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

Sources & evidence

ORD record
ord-00de00cd59a8448982444aeace15829c
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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