Morpholine → 6-(2,4-Dichloro-phenyl)-3-morpholin-4-yl-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile

HRID 420507Notes

Reaction equation

HRID 420507 reaction equation
Cl[C:2]1[N:6]2[CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[C:9]([C:11]#[N:12])=[CH:10][C:5]2=[N:4][N:3]=1.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:8]1[C:9]([C:11]#[N:12])=[CH:10][C:5]2[N:6]([C:2]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:3][N:4]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 666590733-Chloro-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile

Product 1

HCID 666592086-(2,4-Dichloro-phenyl)-3-morpholin-4-yl-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile

Procedure

A solution of the crude [3-chloro-6-(2,4-dichloro-phenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile (50 mg, 0.148 mmol) in morpholine (1.2 mL) was heated at 110° C. and stirred for 5 h. The reaction mixture was concentrated in vacuum, the remaining residue was suspended in water (10 mL) and extracted with AcOEt (3×5 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated to give the crude 6-(2,4-dichloro-phenyl)-3-morpholin-4-yl-[1,2,4]triazolo[4,3-a]pyridine-7-carbonitrile, which was used without further purification. MS: 374 [M+1+]; HPLC: AtRet=1.94.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. extractionextracted with AcOEt (3×5 mL)
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3deab414eb6f48ffb072f3db709c5895
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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