Vinyl chloroformate → 9-(3-Bromo-4-fluorophenyl)-5,6,7,9-tetrahydrofuro [3,4-b][1,7]naphthyridine-1,8(3h,4h)-dione hydrochloride

HRID 478283Notes

Reaction equation

HRID 478283 reaction equation
C([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[CH2:18][O:19][C:20](=[O:21])[C:13]=3[CH:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Br:29])[CH:23]=3)[C:11]=2[C:10](=[O:30])[CH2:9]1)C1C=CC=CC=1.[Cl:31]C(OC=C)=O>C(Cl)Cl>[ClH:31].[Br:29][C:24]1[CH:23]=[C:22]([CH:12]2[C:11]3[C:10](=[O:30])[CH2:9][NH:8][CH2:17][C:16]=3[NH:15][C:14]3[CH2:18][O:19][C:20](=[O:21])[C:13]2=3)[CH:27]=[CH:26][C:25]=1[F:28]

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 111788566-benzyl-9-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydrofuro[3,4-b][1,7]naphthyridine-1,8(3H,4H)-dione

Product 1

HCID 180009619-(3-Bromo-4-fluorophenyl)-5,6,7,9-tetrahydrofuro [3,4-b][1,7]naphthyridine-1,8(3h,4h)-dione hydrochlorideYield 25.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of product from Example 39B (0.35 g, 0.75 mmol) in methylene chloride (10 ml) was treated with vinyl chloroformate (0.1 mL, 1.2 mmol), stirred at ambient temperature for 16 hours, concentrated to dryness, treated with ethanol (10 mL), treated with 6N HCl (3 mL), refluxed for 5 hours and concentrated to dryness, Purification of the residue on silica gel (10:90:1 ethanol/methylene chloride/saturated ammonium hydroxide) provided the title compound (0.08 g) which was converted the HCl salt.

Workup

  1. concentrationconcentrated to dryness
  2. additiontreated with ethanol (10 mL)
  3. additiontreated with 6N HCl (3 mL)
  4. temperaturerefluxed for 5 hours
  5. concentrationconcentrated to dryness, Purification of the residue on silica gel (10:90:1 ethanol/methylene chloride/saturated ammonium hydroxide)

Sources & evidence

ORD record
ord-d10555bac460478e91ed72e95bac270e
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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