Hydrochloric Acid → HCID 178428429, compound

HRID 2254885Notes

Reaction equation

HRID 2254885 reaction equation
[ClH:1].[CH3:2][C:3]1[C:8]([I:9])=[C:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[N:25]=[N:26][N:27](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:28]=3)=[CH:14][CH:13]=2)[CH:6]=[C:5]([CH3:48])[N:4]=1>ClCCl.CO>[ClH:1].[CH3:2][C:3]1[C:8]([I:9])=[C:7]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:25][N:26]=[N:27][N:28]=3)=[CH:16][CH:17]=2)[CH:6]=[C:5]([CH3:48])[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19742893HCID 19742893, compound

Product 1

HCID 178428429HCID 178428429, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Concentrated hydrochloric acid (0.5 ml) was added to a suspension of 2,6-dimethyl-3-iodo-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methylamino]pyridine (A) (215 mg) in dichloromethane/methanol (4 ml) (1:3 v/v) and the mixture stirred for 30 minutes. Volatile material was removed by evaporation and the residue purified by recrystallisation from methanol to give 2,6-dimethyl-3-iodo-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methylamino]pyridine hydrochloride as a white solid, m.p. 238°-240° C. (decomposition); NMR (d6 -DMSO): 2.4(s,3H), 2.7(s,3H), 4.7(d,2H), 6.6(s,1H), 7.1(d,2H), 7.3(d,2H), 7.4-7.7(m,4H), 8.0(t,1H); mass spectrum (positive fast atom bombardment (+ve FAB), DMSO/nitrobenzyl alcohol): 483(M+H)+ ; microanalysis, found: C,48.1; H,4.1; N,16.1%; C21H19N6I.HCl requires: C,48.6; H,3.9; N,16.2%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue purified by recrystallisation from methanol

Sources & evidence

ORD record
ord-d9f8a469c7764011b07caef9050f9035
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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