Triethylamine → 1-(4,5-Dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-5,5-dimethyl-imidazolidine-2,4-dione

HRID 708243Notes

Reaction equation

HRID 708243 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[N:12]=[C:13]([N:15]4[C:19]([CH3:21])([CH3:20])[C:18](=[O:22])[NH:17][C:16]4=[O:23])[S:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:24]=1.C(N(CC)CC)C>C(O)C.[Pd]>[N:12]1[C:11]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:24][C:6]=3[O:7][CH2:8][CH2:9][C:10]=2[S:14][C:13]=1[N:15]1[C:19]([CH3:20])([CH3:21])[C:18](=[O:22])[NH:17][C:16]1=[O:23]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 582042201-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-5,5-dimethylimidazolidin-2,4-dione

Product 1

HCID 582039421-(4,5-Dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-2-yl)-5,5-dimethyl-imidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 49 mg (0.12 mmol) of 1-(8-Bromo-4,5-dihydrothiazolo[4,5-d]benzo[b]oxepin-2-yl)-5,5-dimethylimidazolidin-2,4-dione from Example 485, and 0.0334 ml (0.24 mmol) of triethylamine in 5 ml of ethanol was hydrogenated over 120 mg of 10% palladium on charcoal at 1 atm for 3 hours. The mixture was filtered through celite and concentrated in vacuum. The residue was purified on 4 g siligal column eluting the product with ethyl acetate gradient in heptane to give 493. Yield 20 mg (51%). MS(ESI+): 330.1

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuum
  3. customThe residue was purified on 4 g siligal column
  4. washeluting the product with ethyl acetate gradient in heptane

Sources & evidence

ORD record
ord-39ecd352d20d4804b098fe1d4c20f492
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

Loading…