Phthalic Anhydride → HCID 136133144, compound

HRID 1046822Notes

Reaction equation

HRID 1046822 reaction equation
[NH2:1][C:2]1[N:24]=[C:5]2[NH:6][C:7]([CH3:23])=[C:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.[C:25]1(=O)[O:30][C:28](=[O:29])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.C(N(CC)CC)C>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([CH:9]2[N:4]3[N:3]=[C:2]([N:1]4[C:28](=[O:29])[C:27]5[C:26](=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:25]4=[O:30])[N:24]=[C:5]3[NH:6][C:7]([CH3:23])=[C:8]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:14]=1)#[N:17]

Participants

6

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 136133146HCID 136133146, compound

Product 1

HCID 136133144HCID 136133144, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

Under argon, ethyl 2-amino-7-(4-cyanophenyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (5.0 g, 15.4 mmol) and phthalic anhydride (3.4 g, 23.1 mmol, 1.5 eq.) were dissolved in a mixture of toluene (400 ml) and pyridine (200 ml), triethylamine (42 μl, 0.3 mmol, 0.2 eq.) was added and the mixture was heated under reflux for 12 h. The reaction mixture was then concentrated under reduced pressure. The residue was taken up in ethyl acetate (600 ml) and extracted twice with saturated sodium bicarbonate solution (150 ml each). The organic phase was washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The crude product was suspended in ethanol (100 ml) and stirred for 12 h, and the solid was then filtered off and dried under high vacuum. This gave 6.67 g (95% of theory) of the title compound.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 12 h
  4. concentrationThe reaction mixture was then concentrated under reduced pressure
  5. extractionextracted twice with saturated sodium bicarbonate solution (150 ml each)
  6. washThe organic phase was washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. filtrationthe solid was then filtered off
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-150e34e066424bae85bbf10d53c266d2
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

Loading…