Reacción #156777

ord-325bc05ae51642279bcd9c58c77c1c4b

Ecuación de reacción

CCN(C(C)C)C(C)C
N,N-diisopropylethylamine
O=C1Nc2cc(CO)cnc2N2CCC[C@@H]12
(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one
CNC(=O)c1ccc(N2CCNCC2)cc1
N-methyl-4-(piperazin-1-yl)benzamide
C[P+](C)(C)CC#N.[I-]
(cyanomethyl)trimethylphosphonium iodide
CNC(=O)c1ccc(N2CCN(Cc3cnc4c(c3)NC(=O)[C@@H]3CCCN43)CC2)cc1
product
CNC(=O)c1ccc(N2CCN(Cc3cnc4c(c3)NC(=O)[C@@H]3CCCN43)CC2)cc1
(S)—N-methyl-4-(4-((6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide

Condiciones de reacción

Temperatura
90°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe crude reaction
  2. 2
    Temperaturawas cooled to RT
  3. 3
    Otrothe mixture was purified via HPLC (55-90, basic)

Procedimiento

(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one (1.500 g, 6.84 mmol), N-methyl-4-(piperazin-1-yl)benzamide (1.500 g, 6.84 mmol), (cyanomethyl)trimethylphosphonium iodide (2.494 g, 10.26 mmol) and N,N-diisopropylethylamine (5.97 ml, 34.2 mmol) were suspended in propiononitrile (Volume: 27.4 ml) and heated in a closed vial at 90° C. The crude reaction was cooled to RT, DMSO (1 ml) was added, and the mixture was purified via HPLC (55-90, basic) to give the product as a white solid.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08822470B2uspto-grants-2014_09