HCID 23660838, compound → HCID 131726820, compound

HRID 900087Notes

Reaction equation

HRID 900087 reaction equation
N1C2C(=CC=CC=2)C(CC2C3N(C(C4C=CC=CC=4)=NN=3)C3C=CC=CC=3N([CH2:31][C:32]([N:34]([CH:43]([CH3:45])[CH3:44])[C:35]3[CH:36]=[N:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=3)=[O:33])C2=O)=C1>CCOC(C)=O>[CH:43]([N:34]([C:35]1[CH:36]=[N:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=1)[C:32](=[O:33])[CH3:31])([CH3:44])[CH3:45]

Participants

3

Reactant 1

HCID 23660838HCID 23660838, compound2×

Product 1

HCID 131726820HCID 131726820, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The racemic product of Step B, 2-[4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide (217 mg, 0.355 mmol), was separated into its enantiomers by high pressure chromatography using a Chiralpak AD column (5 cm×50 cm), eluting with heptane in EtOH (75:12), using a flow rate of 85 mL/minute to give enantiomer 1 having a retention time of 7.04 minutes. The enantiomer was dissolved in EtOAc and the organic layer was washed with water (1×) and brine (1×). The organic extract was dried (MgSO4), filtered and concentrated to provide 85 mg of 2-[4-1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide (enantiomer 1). 1H NMR (CD3OD) δ 8.08 (d, 1H), 7.61 (m, 3H), 7.39-7.53 (m, 6H), 7.25 (d, 1H), 7.14 (m, 2H), 7.00 (t, 1H), 6.90 (m, 3H), 4.78 (m, 1H), 4.54 (m, 1H), 4.11 (m, 1H), 3.95 (s, 3H), 3.89 (t, 1H), 3.68-3.82 (m, 2H), 1.01 (m, 6H); MS 612.9 (M+1), 610.5 (M−1); [α]D21 −79.6 (c 0.325, ethanol).

Workup

  1. washeluting with heptane in EtOH (75:12)
  2. customto give enantiomer 1 having a retention time of 7.04 minutes
  3. washthe organic layer was washed with water (1×) and brine (1×)
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-699dfa536ba3473da6a7b93d7733b679
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

Loading…