Acetic Acid → HCID 178435401, compound

HRID 1587505Notes

Reaction equation

HRID 1587505 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:14][CH3:15])=[N:9][C:10]=2[CH2:12][CH3:13])[N:5]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:30]=[N:31][N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:33]=3)=[CH:19][CH:18]=2)[C:4](=[O:53])[CH:3]=1.CS(C)=[O:56].[OH-].[Na+].C(O)(=O)C>O>[ClH:1].[CH2:12]([C:10]1[N:9]=[C:8]([CH2:14][CH3:15])[CH:7]=[C:6]2[C:11]=1[C:2]([OH:56])=[CH:3][C:4](=[O:53])[N:5]2[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[NH:30][N:31]=[N:32][N:33]=2)=[CH:19][CH:18]=1)[CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 19093663HCID 19093663, compound

Product 1

HCID 178435401HCID 178435401, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-chloro-5,7-diethyl-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one (1.0 g), water (10 ml), DMSO (20 ml) and sodium hydroxide (1 g) was stirred and heated at reflux for one hour. The resulting mixture was diluted with water (50 ml), acidified with acetic acid and then extracted twice with ethyl acetate. The combined extracts were washed with water, saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation to give a solid, which was washed with ether and collected by filtration. A mixture of the solid (0.2 g), methanol (4 ml) and concentrated hydrochloric acid (1 ml) was stirred for one hour and then volatile material was removed by evaporation. The residue was purified by repeated precipitation from a methanolic solution with ether to give 5,7-diethyl-4-hydroxy-1-[ (2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one hydrochloride (0.11 g); m.p. 222°-225° C.; NMR (d6 -DMSO): 1.21(t, 3H), 1.31(t, 3H), 2.93(q, 2H), 3.47(q, 2H), 5.51(s, 2H), 6.21(s, 1H), 7.06(d, 2H), 7.18(d, 2H), 7.4-7.75(complex m, 5H); mass spectrum (+ve FAB, methanol/NBA): 453 (M+H)+ ; microanalysis, found: C, 62.0; H, 5.2; N, 16.7%; C26H24N6O.HCl.H2O requires: C, 61.6; H, 5.3; N, 16.6%.

Workup

  1. temperatureheated
  2. temperatureat reflux for one hour
  3. extractionextracted twice with ethyl acetate
  4. washThe combined extracts were washed with water, saturated sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. customVolatile material was removed by evaporation
  7. customto give a solid, which
  8. washwas washed with ether
  9. filtrationcollected by filtration
  10. additionA mixture of the solid (0.2 g), methanol (4 ml) and concentrated hydrochloric acid (1 ml)
  11. stirringwas stirred for one hour
  12. customvolatile material was removed by evaporation
  13. customThe residue was purified
  14. customprecipitation from a methanolic solution with ether

Sources & evidence

ORD record
ord-4c59b64493ca422da77cf2260e710e4d
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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