Hydrochloric Acid → HCID 178468509, compound

HRID 487388Notes

Reaction equation

HRID 487388 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-1,6-naphthyridine-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-5589ee3e9f7b45c1a46cc502b66502c1
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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