Nitrogen → HCID 86651890, compound

HRID 882915Notes

Reaction equation

HRID 882915 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 (0.68 g, 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 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. A cream precipitate forms which is removed by filtration and the solution is concentrated in vacuo. Purification by reverse phase column chromatography (Isolute™ C18, 0-100% acetonitrile in water with 0.1% NH3) affords the title compound. [M+H]+ 402.

Workup

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

Sources & evidence

ORD record
ord-1cdbc325fb8e4b4aa0c2d4deb4dfb53b
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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