Hydrochloric Acid → 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 hydrochloride

HRID 478265Notes

Reaction equation

HRID 478265 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][N:15](C(OC=C)=O)[CH2:14][C:13]=3[NH:12][C:11]3[CH2:25][CH2:26][CH2:27][S:28](=[O:30])(=[O:29])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:31]>C(O)C>[ClH:31].[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][NH:15][CH2:14][C:13]=3[NH:12][C:11]3[CH2:25][CH2:26][CH2:27][S:28](=[O:30])(=[O:29])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11179488vinyl 10-(3-bromo-4-fluorophenyl)-9-oxo-3,4,6,8,9,10-hexahydro-2H-thiopyrano[3,2-b][1,7]naphthyridine-7(5H)-carboxylate 1,1-dioxide

Product 1

HCID 1800098310-(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 hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product from Example 9B (0.25 g) in ethyl alcohol was treated with 6N HCl (1 mL), refluxed for 2 hours, cooled to ambient temperature and concentrated. The residue was purified by flash chromatography over silica gel (15% ethanol/ammonia saturated methylene chloride) to provide the title compound (0.09 g) as the free base which was converted to the hydrochloride salt.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography over silica gel (15% ethanol/ammonia saturated methylene chloride)

Sources & evidence

ORD record
ord-893b9ca61c8646dfbbca2754efd50ec8
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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