Tetrahydrofuran → HCID 178437535, compound

HRID 412709Notes

Reaction equation

HRID 412709 reaction equation
[NH:1]([C:5]1[CH:34]=[CH:33][C:8]2[NH:9][C:10]([CH:12]([C:14]3[NH:15][C:16]4[CH2:21][CH2:20][N:19](C(OCC5C=CC=CC=5)=O)[CH2:18][C:17]=4[N:32]=3)[CH3:13])=[N:11][C:7]=2[CH:6]=1)[C:2]([NH2:4])=[NH:3].O1CCCC1>[Pd].CO>[NH:15]1[C:16]2[CH2:21][CH2:20][NH:19][CH2:18][C:17]=2[N:32]=[C:14]1[CH:12]([C:10]1[NH:9][C:8]2[CH:33]=[CH:34][C:5]([NH:1][C:2]([NH2:4])=[NH:3])=[CH:6][C:7]=2[N:11]=1)[CH3:13]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 178437537HCID 178437537, compound

Product 1

HCID 178437535HCID 178437535, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture comprising benzyl 2-[1-(5-guanidino-1H-benzoimidazol-2-yl)ethyl]-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate (1.0 g, 2.2 mmol), 10% palladium on carbon (0.5 g), tetrahydrofuran (50 mL) and methanol (50 mL) was hydrogenated at one atmosphere, filtered and concentrated in vacuo to provide N-{2-[1-(4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-2-yl)ethyl]-1H-benzoimidazol-5-yl)-guanidine (0.69 g, 97% yield); LRMS(ESI): Calculated for C16H20N8: 324.4; Found (MH+): 325.2.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac2ce074d99c4b1696af366fc312f877
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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