Dichloromethane → HCID 178435373, compound

HRID 487390Notes

Reaction equation

HRID 487390 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:53]([OH:55])=[O:54])[C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[N:29]=[N:30][N:31](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:32]=2)=[CH:18][CH:17]=1)[CH3:2].[Cl:56]CCl>CO.Cl>[ClH:56].[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:53]([OH:55])=[O:54])[C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[NH:32][N:31]=[N:30][N:29]=2)=[CH:18][CH:17]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 19093675HCID 19093675, compound

Product 1

HCID 178435373HCID 178435373, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

5,7-Diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl]biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridine-3-carboxylic acid (A) (165 mg) was dissolved in a mixture of methanol (4 ml), dichloromethane (1 ml) and concentrated hydrochloric acid (0.1 ml) and the mixture was stirred for 15 minutes. Volatile material was then removed by evaporation. The residue was dissolved in methanol (2 ml) and a solid was precipitated by the addition of ether. The solid was collected by filtration and purified by repeated precipitation from methanolic solution with ether to give 5,7-diethyl-2-oxo-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxylic acid hydrochloride (75 mg) as a solid; NMR (d6 -DMSO+d4 -acetic acid): 1.24(t, 3H), 1.34(t, 3H), 2.89(q, 2H), 3.29(q, 2H), 5.64(s, 2H), 7.1(d, 2H), 7.25(d, 2H), 7.41(s, 1H), 7.45-7.75(complex m, 4H), 8.95(s, 1H); mass spectrum (+ve FAB, methanol/NBA): 481 (M+H)+ ; microanalysis, found: C, 57.8; H, 5.0; N, 14.3%; C27H24N6O3.HCl.2.5H2O.0.1(CH3CO2C2H5) requires: C, 57.6; H, 5.4; N, 14.7%.

Workup

  1. customVolatile material was then removed by evaporation
  2. dissolutionThe residue was dissolved in methanol (2 ml)
  3. customa solid was precipitated by the addition of ether
  4. filtrationThe solid was collected by filtration
  5. custompurified
  6. customprecipitation from methanolic solution with ether

Sources & evidence

ORD record
ord-570388942b274a719fcd9320b8d1b7d3
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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