Hydrochloric Acid → HCID 178421995, compound

HRID 487374Notes

Reaction equation

HRID 487374 reaction equation
[ClH:1].[CH3:2][C:3]1[N:12]=[C:11]([CH3:13])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:51])[N:8]2[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[N:28]=[N:29][N:30](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:31]=2)=[CH:17][CH:16]=1>ClCCl.CO>[ClH:1].[CH3:2][C:3]1[N:12]=[C:11]([CH3:13])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](=[O:51])[N:8]2[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[NH:28][N:29]=[N:30][N:31]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 190937065,7-dimethyl-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one

Product 1

HCID 178421995HCID 178421995, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Concentrated hydrochloric acid (0.3 ml) was added to a solution of 5,7-dimethyl-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one (280 mg) (A) in dichloromethane/methanol (4 ml) (3:1 v/v) and the mixture was stirred for 30 minutes. Volatile material was removed by evaporation and the residue was stirred with ether. The insoluble solid was collected by filtration and recrystallised from ethanol/methanol (1:1 v/v) to give 5,7-dimethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,6-naphthyridin-2(1H)-one hydrochloride (105 mg), as a solid, m.p. 278°-280° C. (decomposition); NMR (d6 -DMSO): 2.68(s,3H), 2.96(s,3H), 5.51(s,2H), 6.94(d,1H), 7.05(d,2H), 7.17(d,2H), 7.45-7.71(m,5H), 8.31(d,1H); mass spectrum (positive fast atom bombardment (+ve FAB), DMSO/methanol/nitrobenzyl alcohol(NBA)): 409(M+H)+ ; microanalysis, found: C, 64.1; H, 4.6; N, 18.7%; C24H20N6O.HCl.0.2H2O requires: C,64.1; H,4.8; N,18.7%.

Workup

  1. customVolatile material was removed by evaporation
  2. stirringthe residue was stirred with ether
  3. filtrationThe insoluble solid was collected by filtration
  4. customrecrystallised from ethanol/methanol (1:1 v/v)

Sources & evidence

ORD record
ord-5bab83c0e57742a8b2e27bd18f5207e2
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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