HCID 24746295, compound → HCID 66789712, compound

HRID 1929425Notes

Reaction equation

HRID 1929425 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[C:14]([CH:23]=[CH2:24])=[CH:15][C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][C:12]=3[O:11][C:10]([CH3:26])([CH3:25])[C:9]2=[O:27])=[CH:4][CH:3]=1.[H][H]>C(O)C.[C].[Pd]>[CH2:23]([C:14]1[C:13]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9](=[O:27])[C:10]([CH3:26])([CH3:25])[O:11][C:12]=2[CH:17]=[C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=1)[CH3:24]

Participants

5

Reactant 2

HCID 24746295HCID 24746295, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66789712HCID 66789712, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-5-vinyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide (compound obtained in Example 156, 200 mg) in ethanol (20 mL) was added 10% palladium-carbon (water content: ca. 50%, 200 mg), and the mixture was stirred under atmospheric pressure of hydrogen at room temperature for 20 hours. The reaction mixture was filtered through a celite pad, and the filtrate was concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent; chloroform→chloroform/ethyl acetate=10/1) to give N-[5-ethyl-4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide (209 mg) as a colorless powder.

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resultant residue was purified by column chromatography on silica gel (Solvent; chloroform→chloroform/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-d3c458e79fc94ddeb861d7b1dc5dcbb3
Source dataset
uspto-grants-2012_05
Patent number
US08188073B2

Reaction notes

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