Hydrochloric Acid → HCID 178436871, compound

HRID 1587823Notes

Reaction equation

HRID 1587823 reaction equation
[ClH:1].[CH2:2]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:32]=3)=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH2:53][CH2:54][OH:55])[N:10]=2)[N:5]=1)[CH3:3]>C(O)C>[ClH:1].[CH2:2]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:52][CH2:53][CH2:54][OH:55])[N:10]=2)[N:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19756350HCID 19756350, compound

Product 1

HCID 178436871HCID 178436871, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Concentrated hydrochloric acid (20 ml) was added to a hot suspension of 2-ethyl-6-(2-hydroxyethoxy)-4-[(2 '-(2-triphenylmethyl2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (A) (6.3 g) in ethanol (60 ml). The resulting solution was allowed to cool and left to stand for 1 hour. Volatile material was removed by evaporation and the residue was triturated with ethanol to give 2-ethyl-6-(2-hydroxyethoxy)-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine hydrochloride (3.8 g), as a white powder, m.p. 180°-181° C.; NMR (d6 -DMSO): 1.4(t,3H), 3.2(q,2H), 3.85(t,2H), 4.5(t,2H), 5.65(s,2H), 7.2(d,2H), 7.5-7.8 (complex m,8H), 8.6(d,1H); 13C NMR: (benzylic CH2) 71.5; mass spectrum (+ve FAB, DMSO/m-nitrobenzyl alcohol (NBA)): 469 (M+H)+ ; microanalysis, found: C, 61.2; H,4.9; N,16.2; H2O, 0.6%; C26H24N6O3.HCl.0.25H2O requires: C,61.3; H,5.0; N,16.5; H2O, 0.9%.

Workup

  1. temperatureto cool
  2. waitleft
  3. customVolatile material was removed by evaporation
  4. customthe residue was triturated with ethanol

Sources & evidence

ORD record
ord-14f8667a05bb44af9d8142d6aa430cca
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

Loading…