Hydrochloric Acid → HCID 178436767, compound

HRID 2254895Notes

Reaction equation

HRID 2254895 reaction equation
Cl.[CH2:2]([C:4]1[CH:9]=[C:8]([N:10]([C:48](=[O:50])[CH3:49])[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:7]=[C:6]([CH2:51][CH3:52])[N:5]=1)[CH3:3]>O1CCOCC1>[CH2:2]([C:4]1[CH:9]=[C:8]([N:10]([C:48](=[O:50])[CH3:49])[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[NH:28][N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[CH:7]=[C:6]([CH2:51][CH3:52])[N:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19742903HCID 19742903, compound

Product 1

HCID 178436767HCID 178436767, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4M Hydrochloric acid (1.5 ml) was added to a solution of 2,6-diethyl-4-[N-acetyl-N-(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methylamino]pyridine (A) (0.67 g) in 1,4-dioxan (10 ml) and the mixture was stirred for 4 hours. Volatile material was removed by evaporation and the residue purified by flash chromatography eluting with dichloromethane/methanol (17:3 v/v) to give 2,6-diethyl-4-[N-acetyl-N-(2'-(1H-tetrazol-5-yl)biphenyl-4yl)methylamino]pyridine as a solid; NMR (d6 -DMSO): 1.17(t, 6H), 1.97(t, 3H), 2.67(q, 4H), 4.89(s, 2H), 6.95(s, 2H), 7.05(q, 4H), 7.55(m, 4H); mass spectrum (+ve FAB, benzyl alcohol/methanol): 449(M+Na)+, 427(M+H)+ ; microanalysis, found: C, 67.8; H, 6.4; N, 18.5%; C25H26N6O.0.125C4H10O requires: C, 67.5; H, 6.5; N, 18.9%.

Workup

  1. customVolatile material was removed by evaporation
  2. customthe residue purified by flash chromatography
  3. washeluting with dichloromethane/methanol (17:3 v/v)

Sources & evidence

ORD record
ord-16408d4d58d447448e53babf5fab8d9d
Source dataset
uspto-grants-1993_08
Patent number
US05236937

Reaction notes

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