HCID 10165245, compound → HCID 10185014, compound

HRID 854362Notes

Reaction equation

HRID 854362 reaction equation
[C:1]([C:5]1[CH:36]=[CH:35][C:8]([C:9]([N:11]2[C@@H:15]([C:16]3[S:20][C:19](Cl)=[N:18][CH:17]=3)[C@@H:14]([C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:13][C@@:12]2([CH2:31][CH:32]([CH3:34])[CH3:33])[C:28]([OH:30])=[O:29])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[C@@H:15]([C:16]3[S:20][CH:19]=[N:18][CH:17]=3)[C@@H:14]([C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)[CH2:13][C@@:12]2([CH2:31][CH:32]([CH3:33])[CH3:34])[C:28]([OH:30])=[O:29])=[O:10])=[CH:35][CH:36]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 10165245HCID 10165245, compound

Product 1

HCID 10185014HCID 10185014, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of Example 27 (40 mg, 0.076 mmol) and 10% palladium on carbon catalyst (40 mg) in ethanol (5 mL) was hydrogenated over 5 days. The catalyst was removed by filtration and washed with ethanol. Following evaporation of the solvent the title compound was purified by reverse phase HPLC on a C18 column using a two-solvent gradient elution with (A) water containing formic acid (0.1%) and (B) acetonitrile-water (95:5 v/v) containing formic acid (0.05%) as the eluents, and analysis of the fractions by electrospray mass spectroscopy.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethanol
  3. customevaporation of the solvent the title compound
  4. customwas purified by reverse phase HPLC on a C18 column
  5. washa two-solvent gradient elution with (A) water
  6. additioncontaining formic acid (0.1%) and (B) acetonitrile-water (95:5 v/v)
  7. additioncontaining formic acid (0.05%) as the eluents, and analysis of the fractions by electrospray mass spectroscopy

Sources & evidence

ORD record
ord-4c159ad349394425b2bc428a27ac2463
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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