Hydrochloric Acid → HCID 178468509, compound

HRID 1587508Notes

Reaction equation

HRID 1587508 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]([O:55][CH2:56][CH3:57])=[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].CO.[ClH:60]>ClCCl>[ClH:60].[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]([O:55][CH2:56][CH3:57])=[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 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 19093674HCID 19093674, compound

Product 1

HCID 178468509HCID 178468509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxylate (A) (0.42 g) was added to a mixture of methanol (5 ml), dichloromethane (1 ml) and concentrated hydrochloric acid (0.15 ml) and the mixture was stirred for 20 minutes. Volatile material was removed by evaporation and the residue was triturated with ether to give a white solid. The solid was purified by dissolution in hot ethanol and precipitation by adding ether to give ethyl 5,7-diethyl-2-oxo-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6naphthyridin-3-carboxylate hydrochloride (0.186 g); NMR (d6 -DMSO): 1.25(t, 3H), 1.32(t, 3H), 1.34(t, 3H), 2.95(q, 2H), 3.35(q, 2H), 4.34(q, 2H), 5.55(s, 2H), 7.07(d, 2H), 7.21(d, 2H), 7.4-7.8(complex m, 6H), 8.7(s, 1H), mass spectrum (+ve FAB, DMSO/NBA): 509 (M+H)+ ; microanalysis, found: C, 62.5; H, 5.6; N, 14.8%; C29H28N6O3.HCl.0.14 (CH3CO2C2H5).0.5 H2O requires: C, 62.6; H, 5.5; N, 14.8%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue was triturated with ether
  3. customto give a white solid
  4. customThe solid was purified by dissolution in hot ethanol
  5. customprecipitation
  6. additionby adding ether

Sources & evidence

ORD record
ord-431a9428548643028117bc5ff9603fa6
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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