Toluene → HCID 20290694, compound

HRID 1413759Notes

Reaction equation

HRID 1413759 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[N:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]2=[N:6]1.C1(C)C=CC=CC=1.[Cl:22][C:23]1[N:28]=[C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:26]=[N:25][CH:24]=1>C(N(CC)CC)C>[ClH:1].[Cl:22][C:23]1[N:28]=[C:27]([N:29]2[CH2:30][CH2:31][N:32]([CH2:2][CH2:3][CH2:4][N:5]3[C:13](=[O:14])[N:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]4=[N:6]3)[CH2:33][CH2:34]2)[CH:26]=[N:25][CH:24]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 1079922-Chloro-6-(1-piperazinyl)pyrazineHCID 130412482-(3-Chloropropyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 20290694HCID 20290694, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 3.2 g. (15.1 mmole) of 2-(3-chloropropyl)-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one in 25 ml. toluene is added 2.4 g. (12.1 mmole) of 6-chloro-2-(1-piperazinyl)pyrazine and 2.1 ml. triethylamine. The mixture is refluxed 3 days under N2, cooled, and filtered to give 1.85 g. of the crude base of the title compound. The crude base is chromatographed on silica gel to give the pure base on elution with 1-2% methanol-chloroform. This material is dissolved in absolute ethanol and the solution treated with anhydrous hydrogen chloride to give tan crystals of title compound, m.p. 243°-245°, dec.

Workup

  1. temperatureThe mixture is refluxed 3 days under N2
  2. temperaturecooled
  3. filtrationfiltered
  4. customto give 1.85 g

Sources & evidence

ORD record
ord-b1b2325b47434ace888c9daeb4c51bc7
Source dataset
uspto-grants-1981_02
Patent number
US04251530

Reaction notes

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