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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 2083749
Notes
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Reaction equation

HRID 2083749 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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-fcfacddeb7a64f1a8161570391ac9bad
Source dataset
uspto-grants-1978_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04086348

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes