HCID 19093678, compound → HCID 19093775, compound

HRID 487387Notes

Reaction equation

HRID 487387 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-0f8061602a1746c8bfbf8f2de0bf3fc1
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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