Ammonium Hydroxide → HCID 19851782, compound

HRID 34918Notes

Reaction equation

HRID 34918 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 (0.6 g) and polyphosphoric acid (ca. 6 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 (4×30 ml). The combined chloroform extracts were dried over magnesium sulphate, concentrated in vacuo and the residue was chromatographed on silica eluted with 7.5% v/v methanol in chloroform and then crystallised under ether to give the title compound (0.12 g), m.p. 164°-166° C.

Workup

  1. temperaturewas heated
  2. customto give a solution of ca. pH 8
  3. extractionextracted with chloroform (4×30 ml)
  4. dry with materialThe combined chloroform extracts were dried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica
  7. washeluted with 7.5% v/v methanol in chloroform
  8. customcrystallised under ether

Sources & evidence

ORD record
ord-918fc6756a0f4c87bff09dbcf1ec4043
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Reaction notes

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