Chloride → 2-[(E)-2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-quinoline-6-carbonitrile

HRID 1505482Notes

Reaction equation

HRID 1505482 reaction equation
[CH3:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:11][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:10]=[C:6]2[C:5]([CH3:31])=[N:4][CH:3]=1.[Cl-].[CH:33]([C:35]1[CH:44]=[CH:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:45]#[N:46])[CH:41]=2)[N:36]=1)=O.O1CCCC1.N12CCCN=C1CCCCC2>>[CH3:1][C:2]1[N:7]2[N:8]=[C:9](/[CH:11]=[CH:33]/[C:35]3[CH:44]=[CH:43][C:42]4[C:37](=[CH:38][CH:39]=[C:40]([C:45]#[N:46])[CH:41]=4)[N:36]=3)[N:10]=[C:6]2[C:5]([CH3:31])=[N:4][CH:3]=1

Participants

6

Reactant 5

HCID 312ChlorideHCID 8028TetrahydrofuranHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59151223(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphoniumHCID 896501752-Formyl-6-quinolinecarbonitrile

Product 1

HCID 896497472-[(E)-2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-quinoline-6-carbonitrile

Procedure

To a suspension of (5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphonium; chloride (0.222 g, 0.483 mmol) and 2-Formyl-quinoline-6-carbonitrile (80 mg, 0.4 mmol) in dry Tetrahydrofuran (6 mL, 80 mmol) was added 1,8-Diazabicyclo[5.4.0]undec-7-ene (66 uL, 0.44 mmol) (reaction mixture turns slightly yellow for a while and precipitation changes character) and the mixture was stirred at room temperature under an atmosphere of Argon overnight. The mixture was rotovaped and the THF was evaporated off. The solid was dissolved in DCM and was chromatographed on silicagel (0-30% MeOH in EtOAc). Pure product 2-[(E)-2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-quinoline-6-carbonitrile precipitates in one of the fractions (10): isolated by filtration. Yield: 6 mg white solid.

Workup

  1. customreaction mixture
  2. customturns slightly yellow for a while and precipitation changes character) and the mixture
  3. customthe THF was evaporated off
  4. dissolutionThe solid was dissolved in DCM
  5. customwas chromatographed on silicagel (0-30% MeOH in EtOAc)
  6. customPure product 2-[(E)-2-(5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-quinoline-6-carbonitrile precipitates in one of the fractions (10)
  7. customisolated by filtration

Sources & evidence

ORD record
ord-a9b629b581584ae482c6cb6c3b83a768
Source dataset
uspto-grants-2015_12
Patent number
US09216986B1

Reaction notes

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