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

HRID 66348Notes

Reaction equation

HRID 66348 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[N:15][CH:16]=[CH:17][CH:18]=4)[CH:13]3[OH: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>[CH2:23]([NH:27][C:28]([O:22][CH:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[C:20](=[O:21])[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

5

Reactant 3

HCID 8110Butyl isocyanate2×HCID 8471Triethylamine2×HCID 227547356-(7-chloro-1,8-naphthyridin-2-yl)-7-hydroxy-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Product 1

HCID 227547617-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-7-hydroxy-5-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 1 hour 30 minutes. n-Butyl isocyanate (7.25 cc.) and triethylamine (0.5 cc.) are then added and heating at the reflux temperature is continued for a further 3 hours. The solution is filtered and the filtrate is concentrated under reduced pressure (40 mm.Hg). The residue obtained is triturated with diisopropyl ether (20 cc.). The solid is filtered off and is recrystallised from acetonitrile (35 cc.) to give 7-n-butylaminocarbonyloxy-6-(7-chloro-1,8-naphthyridin-2-yl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (0.96 g.) melting at 215° C.

Workup

  1. temperatureis heated at the reflux temperature for 1 hour 30 minutes
  2. temperatureheating at the reflux temperature
  3. filtrationThe solution is filtered
  4. concentrationthe filtrate is concentrated under reduced pressure (40 mm.Hg)
  5. customThe residue obtained
  6. customis triturated with diisopropyl ether (20 cc.)
  7. filtrationThe solid is filtered off
  8. customis recrystallised from acetonitrile (35 cc.)

Sources & evidence

ORD record
ord-db1d680b3d424e99837d61fc7980ceee
Source dataset
uspto-grants-1978_12
Patent number
US04131674

Reaction notes

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