Ammonium Hydroxide → HCID 19851782, compound

HRID 34919Notes

Reaction equation

HRID 34919 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:28])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:16]3=[N:17][CH:18]=[C:19]([CH2:21][C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH:20]=[C:15]3N=N2)=[N:6][CH:7]=1.[OH-:29].[NH4+]>>[Br:1][C:2]1[CH:3]=[C:4]([CH3:28])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:16]2[C:15]([OH:29])=[CH:20][C:19]([CH2:21][C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][N:17]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 198517733-[4-(5-Bromo-3-methylpyrid-2-yl)butyl]-6-(pyrid-3-ylmethyl)-3H-1,2,3-Triazolo[5,4-b]pyridine

Product 1

HCID 19851782HCID 19851782, compound

Procedure

A mixture of 3-[4-(5-bromo-3-methylpyrid-2-yl)butyl]-6-(pyrid-3-ylmethyl)3H-1,2,3-triazolo[5,4-b]-pyridine (3.9 g) and polyphosphoric acid (ca. 35 g) was heated with stirring at 190°-200° C. for 40 minutes. The cooled residue was dissolved in aqueous ammonium hydroxide to give a solution of ca. pH 8 and extracted with chloroform (4×100 ml). The combined chloroform extracts were dried over magnesium sulphate, concentrated in vacuo to yield 0.6 g title compound (h) m.p. 162°-5° C. The aqueous fraction was evaporated to dryness to yield a pasty residue, which gave on extraction with hot chloroform a further 0.25 g (h) m.p. 163°-164° C. on evaporation. The residue was then heated under reflux with chloroform for 2 hr. and the chloroform solution was chromatographed on silica gel to yield 1.02 g title compound (i) m.p. 110°-112° c.

Workup

  1. temperaturewas heated
  2. customto give a solution of ca. pH 8
  3. extractionextracted with chloroform (4×100 ml)
  4. dry with materialThe combined chloroform extracts were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c374d1e86f8e4e73aa6d4ea1a1c7d07e
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Reaction notes

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