HCID 178462007, compound → HCID 178462008, compound

HRID 339840Notes

Reaction equation

HRID 339840 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([NH:16][C@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[CH3:18])=[N:10][S:9]2(=[O:27])=[O:26])[CH:5]=[CH:6][CH:7]=1>CO.[Pd]>[CH3:15][C:13]1([CH3:14])[O:12][C:11]([NH:16][C@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH3:18])=[N:10][S:9](=[O:27])(=[O:26])[CH:8]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][CH:3]=1

Participants

4

Reactant 1

HCID 178462007HCID 178462007, compound

Product 1

HCID 178462008HCID 178462008, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under inert gas, 48 mg of [5-(3-bromophenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]oxathiazin-2-yl]-[(S)-1-(2-fluorophenyl)ethyl]amine were initially charged in 5 ml of methanol and, with addition of 22 mg of 10% Pd/C, stirred under a hydrogen atmosphere for 1.75 hours. After filtration to remove the solid residues, the filtrate was freed of the solvent under reduced pressure and the crude product was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined and freed of the organic solvent under reduced pressure, and the aqueous residue was lyophilized. This gave the product (27.8 mg) with a molecular weight of 376.4 g/mol (C19H21FN2O3S); MS (ESI): m/e=377 (M+H+).

Workup

  1. filtrationAfter filtration
  2. customto remove the solid residues
  3. customthe crude product was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-0c78306a9ca84248bf18f9b286f4edd7
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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