HCID 20813978, compound → HCID 20813977, compound

HRID 896386Notes

Reaction equation

HRID 896386 reaction equation
[N:1]([CH2:4][C:5]1[C:13]2[N:12]=[C:11]([CH2:14][N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]([CH:24]([CH3:26])[CH3:25])[C:16]3=[O:27])[N:10]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C:5]1[C:13]2[N:12]=[C:11]([CH2:14][N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]([CH:24]([CH3:25])[CH3:26])[C:16]3=[O:27])[N:10]([CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 20813978HCID 20813978, compound

Product 1

HCID 20813977HCID 20813977, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[4-azidomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (108 mg, 0.250 mmol) and palladium black (10 mg) in methanol (20 mL) was rocked under a hydrogen atmosphere (50 psi) for 3 hrs. The residue obtained after filtration and concentration was purified by preparative HPLC (50-70% B 20 min) to give 1-[4-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one; HCl salt as an off white solid after conversion into the hydrochloric acid salt (49 mg, 44%) along with 1-isopropyl-3-[4-methoxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-1,3-dihydro-benzoimidazol-2-one (4 mg, 3%) as a white solid:

Workup

  1. customfor 3 hrs
  2. customThe residue obtained
  3. filtrationafter filtration and concentration
  4. customwas purified by preparative HPLC (50-70% B 20 min)

Sources & evidence

ORD record
ord-78fd59fe9f7f4016aabeab24d54d60d6
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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