Hydrochloric Acid → HCID 178470020, compound

HRID 1614764Notes

Reaction equation

HRID 1614764 reaction equation
[ClH:1].[CH3:2][C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:29]=[N:30][N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:32]=3)=[CH:18][CH:17]=2)[CH:6]=[C:5]([CH3:52])[N:4]=1>O1CCOCC1>[ClH:1].[CH3:2][C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:32][N:31]=[N:30][N:29]=3)=[CH:20][CH:21]=2)[CH:6]=[C:5]([CH3:52])[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15171324HCID 15171324, compound

Product 1

HCID 178470020HCID 178470020, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6M Hydrochloric acid (10 ml) was added to a solution of ethyl 2,6-dimethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine-3-carboxylate (A) (600 mg) in dioxane (15 ml) and the mixture was stirred for 3 hours. Volatile material was removed by evaporation and the residue stirred for 30 minutes in a mixture of ethanol and ether (1:3 v/v, 20 ml). The insoluble solid was collected by filtration and recrystallised from a mixture of ethanol and methanol (1:1 v/v) to give ethyl 2,6-dimethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine-3-carboxylate hydrochloride (270 mg), as a white powder, m.p. 205° C; NMR (d6 -DMSO, d4 -acetic acid): 1.2(t,3H), 2.6(s,3H), 2.7(s,3H), 4.4(q,2H), 5.5(s,2H), 7.2(d,2H), 7.4(d,2H), 7.55-7.65(m,3H), 7.67-7.75(m,2H); mass spectrum [negative fast atom bombardment (-ve FAB), DMSO/glycerol (GLY)]: 428 (M-H)-, 234, 194; microanalysis, found: C,61.7; H,5.0; N,14.9%; C23H24N5O3.HCl requires: C,61.9; H,5.2; N,15.0%.

Workup

  1. customVolatile material was removed by evaporation
  2. stirringthe residue stirred for 30 minutes in a mixture of ethanol and ether (1:3 v/v, 20 ml)
  3. filtrationThe insoluble solid was collected by filtration
  4. customrecrystallised from a mixture of ethanol and methanol (1:1 v/v)

Sources & evidence

ORD record
ord-d379053f5fdf4bdfadeb89791cefb9c5
Source dataset
uspto-grants-1993_03
Patent number
US05198439

Reaction notes

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