Sodium Hydroxide → 3-[3-(5-Bromo-3-methylpyrid-2-yl)propyl]-6-(3-pyridylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine

HRID 34931Notes

Reaction equation

HRID 34931 reaction equation
[N:1]([O-])=O.[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH3:30])[C:9]([CH2:12][CH2:13][CH2:14][NH:15][C:16]2[C:21]([NH2:22])=[CH:20][C:19]([CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:18][N:17]=2)=[N:10][CH:11]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:5][C:6]1[CH:7]=[C:8]([CH3:30])[C:9]([CH2:12][CH2:13][CH2:14][N:15]2[C:16]3=[N:17][CH:18]=[C:19]([CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:20]=[C:21]3[N:22]=[N:1]2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 198517762-[3-(5-Bromo-3-methylpyrid-2-yl)-propylamino]-3-amino-5-(pyrid-3-ylmethyl)pyridineHCID 23668193Sodium Nitrite

Product 1

HCID 198517903-[3-(5-Bromo-3-methylpyrid-2-yl)propyl]-6-(3-pyridylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridineYield 57%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Sodium nitrite solution (1.02 g in 50 ml water) was added dropwise over 25 minutes to a stirred and cooled solution of 2-[3-(5-bromo-3-methylpyrid-2-yl)-propylamino]-3-amino-5-(pyrid-3-ylmethyl)pyridine (4.7 g) in sulphuric acid (molar, 200 ml) keeping the temperature at 4° C. Reaction was stirred at 4° C. for a further hour and was then left in the fridge overnight and then warmed to room temperature. The reaction mixture was basified to pH 13 with sodium hydroxide solution (10M). Chloroform extraction of the reaction mixture gave the crude product which was then chromatographed on silica in methanol/chloroform 1:19 and then recrystallised from acetonitrile to give the title compound (2.75 g), m.p. 109°-110° C.

Workup

  1. customat 4° C
  2. customReaction
  3. stirringwas stirred at 4° C. for a further hour
  4. extractionChloroform extraction of the reaction mixture
  5. customgave the crude product which
  6. customwas then chromatographed on silica in methanol/chloroform 1:19
  7. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-93638bab93db4f92b51a04ab09b9101d
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Reaction notes

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