Reaktion #638289

Reaktionsgleichung

NaHCO3

1-ethoxy-2-(6-methyl-2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)ethaniminium chloride

1-Ethoxy-2-(6-methyl-2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)ethaniminium Chloride

(2S)-5-(2-aminoethyl)-6-nitro-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one

Intermediate 15

(2S)-5-(2-aminoethyl)-6-nitro-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one

→

title compound

6-Methyl-1-{[(8S)-2′-oxo-1′,2′, 4,5,7,9-hexahydro-1H-spiro[indeno[5,6-d][1,3]diazepine-8,3′-pyrrolo[2,3-b]pyridin]-2-yl]methyl}-4H-imidazo[1,5,4-de]quinoxaline-2,5(1H,6H)-dione

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   Extraktionthe mixture was extracted with EtOAc (100 mL)
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe crude product was purified by silica gel chromatography
8. 8
   Wascheneluting with a gradient of CH2Cl2

Vorschrift

A mixture of 1-ethoxy-2-(6-methyl-2,5-dioxo-5,6-dihydro-4H-imidazo[1,5,4-de]quinoxalin-1(2H)-yl)ethaniminium chloride from Step B (72 mg, 0.22 mmol) and (2S)-5-(2-aminoethyl)-6-nitro-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (73 mg, 0.25 mmol, described in Intermediate 15) in EtOH (7 mL) was heated to 100° C. for 5 min then allowed to cool. The reaction was poured into dilute aqueous NaHCO3 (50 mL) and the mixture was extracted with EtOAc (100 mL). The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 80:20, to give the title compound. MS: 71/Z=520 (M+1) HRMS: m/z=520.2081; calculated m/z=520.2092 for C29H26N7O3.

Quelle