Diisopropylethylamine → 5-Chloro-N-[(1S)-1-cyclopropylethyl]pyrazine-2-carboxamide

HRID 571545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571545
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH:11]1([C@@H:14]([NH2:16])[CH3:15])[CH2:13][CH2:12]1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:16][C@H:14]([CH:11]2[CH2:13][CH2:12]2)[CH3:15])=[O:10])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 4654725-Chloropyrazinoic acidHCID 7363995(S)-1-CyclopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 866757595-Chloro-N-[(1S)-1-cyclopropylethyl]pyrazine-2-carboxamideAusbeute 79,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-chloropyrazine-2-carboxylic acid (0.5 g, 3 mmol), (1S)-1-cyclopropylethanamine (0.30 g, 3.5 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1.8 g, 4.7 mmol) and N,N-diisopropylethylamine (1.6 mL, 9.5 mmol) in methylene chloride (5 mL) was stirred at room temperature overnight (22 h.). The mixture was concentrated under reduced pressure. The residue was was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%) to afford the desired product (0.54 g). LCMS (M+H)+: m/z=226.1.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was was purified by flash chromatography on a silica gel column with methanol in dichloromethylene (0-5%)

Quellen und Nachweise

ORD-Eintrag
ord-4bdb4da925854d9dac69d029cee6add5
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023840B2

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