Ammonia → 7-benzyl-10-(3-bromo-4-fluorophenyl)-3,4,6,7,8,10-hexahydro-2H-thiopyrano[3,2-b][1,7]naphthyridin-9(5H)-one 1,1-dioxide

HRID 635973Notes

Reaction equation

HRID 635973 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:16].[S:17]1(=[O:25])(=[O:24])[CH2:22][CH2:21][CH2:20][C:19](=O)[CH2:18]1.[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH:30]=O>C(O)C>[CH2:1]([N:8]1[CH2:9][C:10]2[NH:16][C:19]3[CH2:20][CH2:21][CH2:22][S:17](=[O:25])(=[O:24])[C:18]=3[CH:30]([C:29]3[CH:32]=[CH:33][C:34]([F:35])=[C:27]([Br:26])[CH:28]=3)[C:11]=2[C:12](=[O:14])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 111381741-Benzylpiperidine-3,5-dioneHCID 11815935Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide

Product 1

HCID 114097537-benzyl-10-(3-bromo-4-fluorophenyl)-3,4,6,7,8,10-hexahydro-2H-thiopyrano[3,2-b][1,7]naphthyridin-9(5H)-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of N-benzylpiperidine-3,5-dione (Ziegler, J. Amer. Chem. Soc. (1973), 95, 7458-7464) (0.55 g, 2.5 mmol) in ethyl alcohol (5 mL) was treated with 2.0M ammonia in ethyl alcohol (1.25 mL, 2.5 mmol), stirred for 30 minutes in a sealed tube, treated with tetrahydrothiopyran-3-one-1,1-dioxide (0.36 g, 2.5 mmol), treated with 3-bromo-4-fluorobenzaldehyde (0.51 g, 2.5 mmol), stirred at 75° for 48 hours, cooled and concentrated. The residue was purified by flash chromatography over silica gel (5% ethanol/methylene chloride) to provide the title compound (0.50 g).

Workup

  1. stirringstirred at 75° for 48 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography over silica gel (5% ethanol/methylene chloride)

Sources & evidence

ORD record
ord-239cf5a3af184cf9980db90686426a9f
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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