Butyl isocyanate → 5-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

HRID 2083747Notes

Reaction equation

HRID 2083747 reaction equation
[CH2:1]([N:5]=[C:6]=[O:7])[CH2:2][CH2:3][CH3:4].[Cl:8][C:9]1[N:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([N:19]3[CH:27]([OH:28])[C:26]4[C:21](=[N:22][CH:23]=[CH:24][N:25]=4)[C:20]3=[O:29])=[N:16]2)=[CH:11][CH:10]=1>C(#N)C.C(Cl)Cl>[CH2:1]([NH:5][C:6]([O:28][CH:27]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[C:20](=[O:29])[N:19]1[C:15]1[CH:14]=[CH:13][C:12]2[C:17](=[N:18][C:9]([Cl:8])=[CH:10][CH:11]=2)[N:16]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 64531286-(7-chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one

Product 1

HCID 227547395-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazineYield 50.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

n-Butyl isocyanate (5 g.) is added to a suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-5-hydroxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (7.8 g.) in anhydrous acetonitrile (156 cc.) and the mixture is heated at the reflux temperature for 7 hours. The insoluble product is filtered off and washed with anhydrous acetonitrile (2 × 10 cc.). The product obtained is dissolved in methylene chloride (430 cc.) and the resulting solution is washed by successive decantations with 0.1N sodium hydroxide solution (85 cc.) and water (85 cc.). After drying, the organic phase is concentrated to dryness under reduced pressure (20 mm.Hg). Recrystallisation of the residue obtained, from acetonitrile (230 cc.), gives 5-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (5.2 g.) melting at 264° C.

Workup

  1. temperaturethe mixture is heated at the reflux temperature for 7 hours
  2. filtrationThe insoluble product is filtered off
  3. washwashed with anhydrous acetonitrile (2 × 10 cc.)
  4. customThe product obtained
  5. washthe resulting solution is washed by successive decantations with 0.1N sodium hydroxide solution (85 cc.) and water (85 cc.)
  6. customAfter drying
  7. concentrationthe organic phase is concentrated to dryness under reduced pressure (20 mm.Hg)
  8. customRecrystallisation of the residue
  9. customobtained, from acetonitrile (230 cc.)

Sources & evidence

ORD record
ord-e0ef326573e647ebb76127940a1d1a16
Source dataset
uspto-grants-1978_04
Patent number
US04086348

Reaction notes

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