HCID 22349401, compound → HCID 20813975, compound

HRID 896388Notes

Reaction equation

HRID 896388 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][CH:26]=[C:27]([CH2:28][C:29]#[N:30])[C:16]=3[N:15]=2)[C:5]1=[O:31])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:30][CH2:29][CH2:28][C:27]1[C:16]2[N:15]=[C:14]([CH2:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:4]([CH:1]([CH3:2])[CH3:3])[C:5]3=[O:31])[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]=2[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 22349401HCID 22349401, compound

Product 1

HCID 20813975HCID 20813975, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of [2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-4-yl]-acetonitrile (51 mg, 0.12 mmol) and 10% Pd/C (9 mg) in methanol (20 mL) was rocked in a Parr shaker under a hydrogen atmosphere (40 psi) for 15 hrs. The catalyst was removed by filtration and the filtrate concentrated. The residue was purified by preparative HPLC (30-100% B) to give 1-[4-(2-amino-ethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one; HCl salt as the TFA salt, that was converted into the HCl salt by treatment with excess acetyl chloride in methanol, followed by removal of the volatiles in vacuo: 5 mg, 9% as a white solid.

Workup

  1. customfor 15 hrs
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated
  4. customThe residue was purified by preparative HPLC (30-100% B)

Sources & evidence

ORD record
ord-fe69e98da45c428faa6e447e8ad8595a
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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