HCID 59707057, compound → HCID 59707066, compound

HRID 221962Notes

Reaction equation

HRID 221962 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][C:8]([CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=3)[C:11]2=[O:29])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:31][CH:30]=3)[C:11]2=[O:29])=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 59707057HCID 59707057, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59707066HCID 59707066, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-charcoal (5%, 650 mg) was added to a solution of 1-(4-tert-butylbenzyl)-3-(4-nitrobenzyl)-1,3-dihydrobenzimidazol-2-one (P) (1.13 g, 2.73 mmol) in abs. MeOH (60 mL). The reaction mixture was subjected to a hydrogen pressure of 3 bar for 20 min at RT. The catalyst was separated by filtration, and the filtrate was concentrated in vacuo. The residue was taken up in EtOAc (10 mL) and filtered through a frit with kieselguhr (layer thickness 1 cm). The frit was washed with ethyl acetate (4×20 mL). The desired product 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-1,3-dihydrobenzimidazol-2-one (Q) was obtained in a yield of 960 mg (91% of theory). The corresponding hydrochloride was obtained by reaction of 1-(4-aminobenzyl)-3-(4-tert-butylbenzyl)-1,3-dihydrobenzimidazol-2-one (Q) with chlorotrimethylsilane (1 mL, 7.9 mmol) in DCM (50 mL). The reaction mixture was stirred over a period of 17 h without exclusion of moisture, and the resulting solid matter was separated with the aid of a frit and then dried. The hydrochloride was obtained as solid matter (750 mg, 68% of theory, mp: 198-219° C.).

Workup

  1. customThe catalyst was separated by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. filtrationfiltered through a frit with kieselguhr (layer thickness 1 cm)
  4. washThe frit was washed with ethyl acetate (4×20 mL)

Sources & evidence

ORD record
ord-1977b8131d8d479eb49815b6d8c79c71
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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