Tert-Butylamine → 2-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246632
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6385Tert-ButylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 866779952-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The mixture of 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (320 mg, 0.9 mmol), tert-butylamine (0.5 mL, 4.5 mmol) and HATU (684 mg, 1.8 mmol) in 50 mL of dry THF was stirred for 4 hours at room temperature. The reaction mixture was evaporated to dryness, then the residue was suspended in 50 mL of 0.5 N HCl, product extracted with ethyl acetate (50 mL×3), dried with sodium sulfate, filtered and concentrated to give 2-bromo-N-tert-butyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (258 mg, crude), material used in the next step without further purification. LCMS: (M+H)+=297/299; (M+Na)+=319/321.

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness
  2. extractionproduct extracted with ethyl acetate (50 mL×3)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5cfbd0d7f71245b88501f8164d254a8c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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