Octahydropyrrolo(1,2-a)pyrazine → HCID 178489799, Verbindung

HRID 16817

Reaktionsgleichung

Reaktionsgleichung von HRID 16817
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][CH2:8][CH2:9][CH:2]12.Cl[C:11]1[N:12]=[CH:13][C:14]([C:17]([NH:19][C:20]2[NH:21][N:22]=[C:23]([CH2:25][CH2:26][C:27]3[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[CH:28]=3)[CH:24]=2)=[O:18])=[N:15][CH:16]=1>CS(C)=O>[CH2:1]1[CH:2]2[CH2:9][CH2:8][CH2:7][N:3]2[CH2:4][CH2:5][N:6]1[C:11]1[N:12]=[CH:13][C:14]([C:17]([NH:19][C:20]2[NH:21][N:22]=[C:23]([CH2:25][CH2:26][C:27]3[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[CH:28]=3)[CH:24]=2)=[O:18])=[N:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 558578Octahydropyrrolo(1,2-a)pyrazineHCID 178489782HCID 178489782, Verbindung

Produkt 1

HCID 178489799HCID 178489799, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1,2,3,4,6,7,8,8a-Octahydropyrrolo[1,2-a]pyrazine (429 mg, 3.40 mmol) was added in one portion to 5-chloro-N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]pyrazine-2-carboxamide (659 mg, 1.70 mmol) in anhydrous dimethylsulfoxide (1.70 ml) at 25° C. The resulting solution was stirred at 100° C. for 18 h. The crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH to afford impure material. The concentrated eluent was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% TFA) and MeCN as eluents. The material was then put through basic HPLC to obtain the free base. Fractions containing the desired compound were evaporated to dryness to afford the title compound (438 mg, 54%) as a cream solid.

Aufarbeitung

  1. customThe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customto afford impure material
  4. customThe concentrated eluent was purified by preparative HPLC
  5. customto obtain the free base

Quellen und Nachweise

ORD-Eintrag
ord-40cc418693dd4867bcbb8a674e679e35
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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