Hydrochloric Acid → HCID 178435372, compound

HRID 487375Notes

Reaction equation

HRID 487375 reaction equation
[ClH:1].[CH2:2]([C:4]1[N:13]=[C:12]([CH2:14][CH3:15])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:53])[N:9]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[N:30]=[N:31][N:32](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:33]=2)=[CH:19][CH:18]=1)[CH3:3]>CO>[ClH:1].[CH2:2]([C:4]1[N:13]=[C:12]([CH2:14][CH3:15])[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:53])[N:9]2[CH2:16][C:17]1[CH:18]=[CH:19][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:21][CH:22]=1)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19093705HCID 19093705, compound

Product 1

HCID 178435372HCID 178435372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (0.5 ml) was added to a solution of 5,7-diethyl-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one (500 mg) (A) in methanol (5 ml) and the mixture was stirred for 30 minutes. Volatile material was removed by evaporation and the residue was dissolved in hot ethanol. The solution was cooled, evaporated to small volume and the product collected by filtration to give 5,7-diethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one hydrochloride (230 mg), as a solid, m.p. 265°-269° C. (decomposition); NMR (d6 -DMSO): 1.15-1.4(m,6H), 2.95(q,2H), 3.35(q,2H), 5.55(s,2H), 6.9(d,1H), 7.05(d,2H), 7.2(d,2H), 7.4-7.75(m,5H), 8.45(d,1H); mass spectrum (+ve FAB, methanol/NBA): 459(M+Na)+, 437(M+H)+ ; microanalysis, found: C, 64.8; H, 5.4; N, 17.4; C26H24N6O.HCl.0.5H2O requires C, 64.8; H, 5.4; N, 17.4%.

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in hot ethanol
  3. temperatureThe solution was cooled
  4. customevaporated to small volume
  5. filtrationthe product collected by filtration

Sources & evidence

ORD record
ord-5bfdfe14a47d4b9fbe035d90bb9c332e
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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