Hydrochloric Acid → 5-(3-Bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1h-pyrano[3,4-b][1,7]naphthyridine-4,6(3h,7h)-dione hydrochloride

HRID 478269Notes

Reaction equation

HRID 478269 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][O:26][CH2:27][C:28](=[O:29])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].[ClH:30]>C(O)C>[ClH:30].[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][O:26][CH2:27][C:28](=[O:29])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18000982vinyl 5-(3-bromo-4-fluorophenyl)-4,6-dioxo-4,5,6,7,9,10-hexahydro-1H-pyrano[3,4-b][1,7]naphthyridine-8(3H)-carboxylate

Product 1

HCID 180009955-(3-Bromo-4-fluorophenyl)-5,8,9,10-tetrahydro-1h-pyrano[3,4-b][1,7]naphthyridine-4,6(3h,7h)-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Example 24B in ethanol (10 mL) was treated with 6N HCl (5 mL), refluxed for 3 hours and concentrated. Purification by flash chromatography over silica gel (10% methanol/ammonia saturated methylene chloride) provided the title compound (0.080 g) which was converted to the hydrochloride salt.

Workup

  1. temperaturerefluxed for 3 hours
  2. concentrationconcentrated
  3. customPurification by flash chromatography over silica gel (10% methanol/ammonia saturated methylene chloride)

Sources & evidence

ORD record
ord-58d2e4ad5c7548019bc21080076750f6
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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