HCID 178435594, compound → HCID 178525129, compound

HRID 1615108Notes

Reaction equation

HRID 1615108 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([C:26]#[CH:27])=[CH:25][C:19]=2[N:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CC1C=CC(C(C)C)=CC=1.CC1C=CC(C(C)C)=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24](/[CH:26]=[CH:27]/[C:27]#[C:26][C:24]3[CH:23]=[CH:22][C:20]4[NH:21][C:17]([C@@H:12]5[CH2:13][CH2:14][CH2:15][CH2:16][N:11]5[C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[O:10])=[N:18][C:19]=4[CH:25]=3)=[CH:25][C:19]=2[N:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 178435594HCID 178435594, compound

Product 1

HCID 178525129HCID 178525129, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 10908223Dichloro(p-cymene)ruthenium(II) dimerCatalyst

Procedure

A mixture of (S)-2-(5-ethynyl-1H-benzoimidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester (41 mg, 0.115 mmol) and dichloro(p-cymene)ruthenium(II) dimer (5 mg) is purged with N2. AcOH (1 mL) is added and the mixture is stirred at room temperature overnight and concentrated in vacuum to dryness. The residue is purified by flash column chromatography on silica gel (EtOAc/hexanes 5% to 100%) and repurified by reverse phase HPLC using a gradient of CH3CN/water to afford the title compound (5.9 mg, 7%).

Workup

  1. customis purged with N2
  2. additionAcOH (1 mL) is added
  3. concentrationconcentrated in vacuum to dryness
  4. customThe residue is purified by flash column chromatography on silica gel (EtOAc/hexanes 5% to 100%)
  5. customrepurified by reverse phase HPLC

Sources & evidence

ORD record
ord-c0145deeefbc413db94542f621c5172d
Source dataset
uspto-grants-2014_07
Patent number
US08765731B2

Reaction notes

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