3-Butyn-2-amine, 2-methyl- → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(2-methylbut-3-yn-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246577

Reaktionsgleichung

Reaktionsgleichung von HRID 246577
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:21]([OH:23])=O)=[CH:19][NH:20][C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH3:24][C:25]([NH2:29])([C:27]#[CH:28])[CH3:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:17]=[C:16]4[C:18]([C:21]([NH:29][C:25]([CH3:26])([C:27]#[CH:28])[CH3:24])=[O:23])=[CH:19][NH:20][C:15]4=[N:14][CH:13]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 763193-Butyn-2-amine, 2-methyl-HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 866779922-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(2-methylbut-3-yn-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamideAusbeute 23,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (70 mg, 0.225 mmol), 2-methylbut-3-yn-2-amine (28 mg, 0.338 mmol), HATU (171 mg, 0.45 mmol) and DIEA (58 mg, 0.45 mmol) in DMF (3 mL) was stirred at room temperature for 16 hours. Then the mixture was poured into water and filtered to give the crude product. The crude compound was then washed with MeOH to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-N-(2-methylbut-3-yn-2-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (20 mg, 23.5%).

Aufarbeitung

  1. filtrationfiltered
  2. customto give the crude product
  3. washThe crude compound was then washed with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-f3f52c0666b94a278cb018860fd14320
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

Verknüpfte Notizen

Wird geladen…