Nitrogen → HCID 86651890, compound

HRID 1183039Notes

Reaction equation

HRID 1183039 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C@H:8]([CH2:24][NH:25][C:26]([C:28]1[C:33]([NH2:34])=[N:32][C:31]([NH2:35])=[C:30]([Cl:36])[N:29]=1)=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13]C(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].N#N.[H][H]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:37])[NH:7][C@H:8]([CH2:24][NH:25][C:26]([C:28]1[C:33]([NH2:34])=[N:32][C:31]([NH2:35])=[C:30]([Cl:36])[N:29]=1)=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 947NitrogenHCID 86651898HCID 86651898, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86651890HCID 86651890, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of ((S)-5-benzyloxycarbonylamino-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (680 mg, 1.27 mmol) in EtOH (20 mL) under an inert atmosphere of N2 is treated with activated palladium on charcoal (10%). The reaction mixture is then placed under a positive pressure of hydrogen and stirred at RT. After 3 h, the mixture is purged with N2 and the catalyst is removed by filtration through Celite® (filter material). The filtrate is concentrated in vacuo and the resulting colourless oil is dissolved in MeOH (10 mL) and allowed to stand at RT overnight. The cream precipitate which forms is removed by filtration and the solution is concentrated in vacuo. The resulting crude product is purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% NH3) to afford the title compound. [M+H]+ 402.

Workup

  1. customthe mixture is purged with N2
  2. customthe catalyst is removed by filtration through Celite® (filter material)
  3. concentrationThe filtrate is concentrated in vacuo
  4. dissolutionthe resulting colourless oil is dissolved in MeOH (10 mL)
  5. waitto stand at RT overnight
  6. customThe cream precipitate which forms is removed by filtration
  7. concentrationthe solution is concentrated in vacuo
  8. customThe resulting crude product is purified by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% NH3)

Sources & evidence

ORD record
ord-48bd3025ed4c4c42a35a3b0dde57c93f
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

Loading…