Water → HCID 19851783, compound

HRID 1607050Notes

Reaction equation

HRID 1607050 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:27])[C:5]([CH2:8][CH2:9][CH2:10][N:11]2[C:15]3=[N:16][CH:17]=[C:18]([CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=[C:14]3N=N2)=[N:6][CH:7]=1.[OH2:28].[OH-].[NH4+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:27])[C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:15]2[C:14]([OH:28])=[CH:19][C:18]([CH2:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][N:16]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 198517903-[3-(5-Bromo-3-methylpyrid-2-yl)propyl]-6-(3-pyridylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine

Product 1

HCID 19851783HCID 19851783, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-[3-(5-Bromo-3-methylpyrid-2-yl)propyl]-6-(3-pyridylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine (2.68 g) was added in portions over 15 minutes to hot (190°-200° C.) stirred polyphosphoric acid (10.45 g). The stirred reaction was heated at 190°-200° C. for a further 45 minutes, water (20 ml) was added to the hot reaction mixture, the solution was neutralised with concentrated ammonium hydroxide and allowed to cool. The pH was then raised to 10, chloroform extraction of the aqueous mixture gave a brown solid. This solid was recrystallised from ethanol/ether giving buff crystals (1.64 g). These were chromatographed on silica in methanol/chloroform 1:9, the product was then recrystallised from chloroform/petroleum ether (40°-60° C.) to give the title compound (1.4 g) (off-white crystals), m.p. 141°-143° C.

Workup

  1. customThe stirred reaction
  2. temperaturewas heated at 190°-200° C. for a further 45 minutes
  3. temperatureto cool
  4. customgave a brown solid
  5. customThis solid was recrystallised from ethanol/ether giving buff crystals (1.64 g)
  6. customThese were chromatographed on silica in methanol/chloroform 1:9
  7. customthe product was then recrystallised from chloroform/petroleum ether (40°-60° C.)

Sources & evidence

ORD record
ord-61248afb485c4d9b994351cf874981a2
Source dataset
uspto-grants-1989_09
Patent number
US04863933

Reaction notes

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