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 635992Notes

Reaction equation

HRID 635992 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
  6. customPurification of the residue on silica gel (10:90:1 ethanol/methylene chloride/saturated ammonium hydroxide)

Sources & evidence

ORD record
ord-44e5682f390c441489fa3996fbc3ec5d
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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