Triethylamine → 7-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

HRID 1889062

Reaktionsgleichung

Reaktionsgleichung von HRID 1889062
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:11]3[CH2:12][CH2:13][NH:14][CH2:15][C:10]3=[N:9][N:8]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:23][C:24]1[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:23][C:24]1[C:32]([C:33]([F:35])([F:36])[F:34])=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([N:14]1[CH2:13][CH2:12][N:11]2[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[N:8][N:9]=[C:10]2[CH2:15]1)=[O:27]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 38276332-Chloro-3-(trifluoromethyl)benzoyl chlorideHCID 625876923-(Pyridin-4-yl)-5,6,7,8-tetrahydro-(1,2,4)triazolo(4,3-a)pyrazine

Produkt 1

HCID 665991747-{[2-Chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-(4-Pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine (0.150 g, 0.745 mmol, e.g. prepared as described below) was treated with N,N-dimethylformamide (DMF) (3 mL) and cooled to 0° C. Triethylamine (0.109 mL, 0.783 mmol) and N,N-dimethyl-4-pyridinamine (DMAP) (0.009 g, 0.075 mmol) were added at 0° C. under argon and the mixture was stirred for 5 minutes; then 2-chloro-3-(trifluoromethyl)benzoyl chloride (0.199 g, 0.820 mmol, commercially available e.g. from Apollo Scientific or Shanghai FWD Chemicals) was added. The reaction mixture was kept at 0° C. for ½ hour. The reaction was quenched with water, extracted with ethyl acetate (two extractions), and the combined organic phases were washed with a saturated sodium bicarbonate solution, followed by water (four washes). The organic phase was dried, and evaporated to give a yellow oil. The residue was purified by silica gel chromatography using 0-20% of methanol in Dichloromethane as the eluent and then triturated with diethyl ether to give 7-{[2-chloro-3-(trifluoromethyl)phenyl]carbonyl}-3-(4-pyridinyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine as a white solid. The solid was dried at 50° C. on the high vacuum for 1 day.

Aufarbeitung

  1. waitThe reaction mixture was kept at 0° C. for ½ hour
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate (two extractions)
  4. washthe combined organic phases were washed with a saturated sodium bicarbonate solution
  5. customThe organic phase was dried
  6. customevaporated
  7. customto give a yellow oil
  8. customThe residue was purified by silica gel chromatography
  9. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7132843910b64550a81d28be88c40845
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501946B2

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