Dimethylformamide → 7-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

HRID 62460

Reaktionsgleichung

Reaktionsgleichung von HRID 62460
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([N:11]3[CH2:16][CH2:15][N:14]4[C:17]([C:20]([F:23])([F:22])[F:21])=[N:18][N:19]=[C:13]4[CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.CN(C=O)C.[Br:29]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:29][C:10]1[N:9]=[C:8]([N:11]2[CH2:16][CH2:15][N:14]3[C:17]([C:20]([F:23])([F:21])[F:22])=[N:18][N:19]=[C:13]3[CH2:12]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([Cl:1])[C:3]=12

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 866746537-(8-Chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine

Produkt 1

HCID 903040957-(1-Bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 100 ml one neck round bottom flask was charged with 7-(8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (540 mg, 1.571 mmol) along with DMF (5 ml). The mixture was stirred and 1-bromopyrrolidine-2,5-dione (308 mg, 1.728 mmol) was added in on batch. The resulting reaction mixture was then stirred at room temperature for 18 hrs overnight. The mixture was diluted with ethyl acetate and washed with NaHCO3 (sat), water, dried over MgSO4, filtered and concentrated. The residue was purified by MPLC (24 g silica gel, 50% to 100% ethyl acetate in hexanes, 18 CV) to afford light color solid product 7-(1-bromo-8-chloroimidazo[1,5-a]pyrazin-3-yl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (595 mg, 1.408 mmol, 90% yield). LC-MS: C12H8BrClF3N7, 421. found 422.02 [M+H]+, RT=1.30 min.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. stirringwas then stirred at room temperature for 18 hrs overnight
  3. washwashed with NaHCO3 (sat), water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC (24 g silica gel, 50% to 100% ethyl acetate in hexanes, 18 CV)

Quellen und Nachweise

ORD-Eintrag
ord-444e34bae86449a4b117386bfc52fdce
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446130B2

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