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

HRID 66347Notes

Reaction equation

HRID 66347 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[CH2:23]([N:27]=[C:28]=[O:29])[CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(#N)C.C(N(CC)CC)C>[CH2:23]([NH:27][C:28]([O:21][CH:20]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:22])[N:12]1[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[N:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)=[O:29])[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 8110Butyl isocyanate2×HCID 8471TriethylamineHCID 22754749HCID 22754749, compound

Product 1

HCID 227547335-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-5-hydroxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (1 g.) in acetonitrile (100 cc.) containing n-butyl isocyanate (7.25 cc.) and triethylamine (0.5 cc.) is heated at the reflux temperature for 3 hours. n-Butyl isocyanate (2.9 cc.) and triethylamine (2 drops) are then added and heating at the reflux temperature is continued for a further 30 minutes. After concentrating the mixture to dryness under reduced pressure (40 mm.Hg), the residue is triturated with diisopropyl ether (10 cc.). The precipitate is filtered off and recrystallised from acetonitrile (41 cc.) to give 5-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (0.8 g.) melting at 215° C.

Workup

  1. temperatureis heated at the reflux temperature for 3 hours
  2. temperatureheating at the reflux temperature
  3. concentrationAfter concentrating the mixture to dryness under reduced pressure (40 mm.Hg)
  4. customthe residue is triturated with diisopropyl ether (10 cc.)
  5. filtrationThe precipitate is filtered off
  6. customrecrystallised from acetonitrile (41 cc.)

Sources & evidence

ORD record
ord-498db6be56e54d0d9a677de19029d804
Source dataset
uspto-grants-1978_12
Patent number
US04131674

Reaction notes

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