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Diisopropylethylamine → 2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-cyano-2-methyl-ethyl)-amide

HRID 246128
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 246128
FC(F)(F)C(O)=O.[NH2:8][CH2:9][C@@H:10]([CH3:13])[C:11]#[N:12].[F:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([C:25]3[N:26]=[C:27]4[C:33]([C:34](O)=[O:35])=[CH:32][N:31]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:28]4=[N:29][CH:30]=3)=[N:20][N:21]2[CH3:24])=[CH:17][CH:16]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(#N)C.C(OCC)(=O)C.O>[C:11]([C@H:10]([CH3:13])[CH2:9][NH:8][C:34]([C:33]1[C:27]2[C:28](=[N:29][CH:30]=[C:25]([C:19]3[C:18]4[C:22](=[CH:23][C:15]([F:14])=[CH:16][CH:17]=4)[N:21]([CH3:24])[N:20]=3)[N:26]=2)[N:31]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:32]=1)=[O:35])#[N:12]
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Komponenten

8

Edukt 4

HCID 81531Diisopropylethylamine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 712796202-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 86677952(R)-3-amino-2-methyl-propionitrile trifluoroacetate

Produkt 1

HCID 71285858
2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-cyano-2-methyl-ethyl)-amide
Ausbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-3-Amino-2-methyl-propionitrile trifluoroacetate (crude from Step 3) was dissolved in acetonitrile (2.8 ml) to which was then added 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (80 mg, 0.18 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (70 mg, 0.22 mmol) and N,N-diisopropylethylamine (0.11 ml, 0.63 mmol). The reaction was stirred at room temperature for 18 h. Additional O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (50 mg, 0.16 mmol) and N,N-diisopropylethylamine (0.11 ml, 0.63 mmol) were added and stirring was continued for 24 h. Water and ethyl acetate were added. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with sodium chloride solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography (methanol/dichloromethane) to afford 33 mg (36%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((R)-2-cyano-2-methyl-ethyl)-amide. (M+Na)+=530.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 24 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customAfter evaporation
  8. customthe residue was purified by silica gel chromatography (methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-526a2114f66847ee97e953a6145bde36
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08658646B2

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