Hydrochloric Acid → HCID 178428934, compound

HRID 1769068Notes

Reaction equation

HRID 1769068 reaction equation
[ClH:1].[CH3:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:30]=[N:31][N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:33]=3)=[CH:19][CH:18]=2)[CH:6]=[C:5]([CH3:53])[N:4]=1>O1CCOCC1>[ClH:1].[ClH:1].[CH3:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[NH:30][N:31]=[N:32][N:33]=3)=[CH:19][CH:18]=2)[CH:6]=[C:5]([CH3:53])[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18946463HCID 18946463, compound

Product 1

HCID 178428934HCID 178428934, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6M Hydrochloric acid (1 ml) was added to a solution of 2,6-dimethyl-3-(4-pyridyl)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (A) (800 mg) in dioxan (20 ml) and the mixture was stirred for 3 hours. Volatile material was removed by evaporation and the residue triturated with ether. The ether was separated and the residue was dissolved in methanol. Ether was added to precipitate the product and the solvent was again separated. The residue was then triturated with ether to give 2,6-dimethyl-3-(4-pyridyl)-4-[(2'(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine dihydochloride (0.51 g), as a solid, m.p. 180° C. (decomposition); NMR (d6 -DMSO, d4 -acetic acid): 2.4(s,3H), 2.75(s,3H), 5.45(s,2H), 7.1(d,2H), 7.25(d,2H), 7.5-7.8 (complex m,5H), 8.0(d,2H), 9.0(d,2H); mass spectrum (positive fast atom bombardment (+ve FAB) DMSO/nitrobenzyl alcohol): 869.4 (2M+H)+ ; microanalysis, found: C,56.7; H,5.3; N,14.9; H2O,8%; C26H22N6O.2HCl.2.5H2O0.2(C2H5)2O requires C,56.7; H,5.5; N,14.8%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue triturated with ether
  3. customThe ether was separated
  4. dissolutionthe residue was dissolved in methanol
  5. additionEther was added
  6. customto precipitate the product
  7. customthe solvent was again separated
  8. customThe residue was then triturated with ether

Sources & evidence

ORD record
ord-5851ea9f06fc421a955e4f267361b481
Source dataset
uspto-grants-1995_01
Patent number
US05380730

Reaction notes

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