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

HRID 478266Notes

Reaction equation

HRID 478266 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:24])(=[O:23])[CH2:21][CH2:20][C:19](=O)[CH2:18]1.[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[F:34])[CH:29]=O>C(O)C>[CH2:1]([N:8]1[CH2:9][C:10]2[NH:16][C:19]3[CH2:20][CH2:21][S:17](=[O:24])(=[O:23])[C:18]=3[CH:29]([C:28]3[CH:31]=[CH:32][C:33]([F:34])=[C:26]([Br:25])[CH:27]=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 5150067dihydrothiophen-3(2H)-one 1,1-dioxideHCID 111381741-Benzylpiperidine-3,5-dione

Product 1

HCID 113755316-benzyl-9-(3-bromo-4-fluorophenyl)-2,3,5,6,7,9-hexahydrothieno[3,2-b][1,7]naphthyridin-8(4H)-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 4 hours in a sealed tube, treated with the product from Example 10C (0.33 g, 2.5 mmol), treated with 3-bromo-4-fluorobenzaldehyde (0.51 g, 2.5 mmol), stirred at 75° C. for 48 hours, cooled and concentrated. The residue was purified by flash chromatography over silica gel (5-10% ethanol/methylene chloride) to provide the title compound (0.28 g).]

Workup

  1. stirringstirred at 75° C. for 48 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography over silica gel (5-10% ethanol/methylene chloride)

Sources & evidence

ORD record
ord-192dbbd6ea104b0f8647aaebbb424081
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

Loading…