HCID 19093678, compound → HCID 19093775, compound

HRID 1587507Notes

Reaction equation

HRID 1587507 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:6][C:7](=[O:26])[N:8]2[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)[CH3:2]>O1CCOCC1.O.Cl>[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[C:5]([S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:6][C:7](=[O:26])[N:8]2[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1)[CH3:2]

Participants

5

Reactant 1

HCID 19093678HCID 19093678, compound

Product 1

HCID 19093775HCID 19093775, compoundYield 61.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-[(5,7-diethyl-2-oxo-4-phenylthio-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]benzoate (200 mg) was dissolved in a mixture of dioxan (4 ml), water (1 ml) and concentrated hydrochloric acid (1 ml) and the mixture was heated at reflux for 4 hours. Volatile material was then removed by evaporation and toluene was added to the residue. Volatile material was again removed by evaporation. The solid residue was recrystallised from ethanol/ether to give 4-[(5,7-diethyl-2-oxo-4-phenylthio-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]benzoic acid (120 mg) m.p. 260°-262° C.; NMR (d6 -DMSO): 1.19(t, 3H), 1.51(t, 3H), 2.98(q, 2H), 3.72(q, 2H), 5.56(s, 2H), 5.91(s, 1H), 7.35(d, 2H), 7.47(s, 1H), 7.6-7.8(complex m, 5H), 7.88(d, 2H), mass spectrum (CI, ammonia): 445(M+H)+ ; microanalysis, found: C, 64.5; H, 5.4; N, 5.9%; C26H24N2O3S requires: C, 64.9; H, 5.2; N, 5.8%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. customVolatile material was then removed by evaporation and toluene
  4. additionwas added to the residue
  5. customVolatile material was again removed by evaporation
  6. customThe solid residue was recrystallised from ethanol/ether

Sources & evidence

ORD record
ord-af1cdd51b132434baf7a605b27beaa58
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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