N-methyl-2-pyrrolidone → 4-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-[(3R)-3-hydroxypiperidino]phthalazine hydrochloride

HRID 47291

Reaktionsgleichung

Reaktionsgleichung von HRID 47291
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[C:5]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)=[N:4][N:3]=1.Cl.[OH:26][C@@H:27]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]1.C(N(C(C)C)CC)(C)C.CN1CCCC1=O>C(OCC)(=O)C>[ClH:1].[Cl:24][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[O:22][CH3:23])[CH2:15][NH:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=2)[C:2]([N:29]2[CH2:30][CH2:31][CH2:32][C@@H:27]([OH:26])[CH2:28]2)=[N:3][N:4]=1

Komponenten

6

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 2759333(3R)-piperidin-3-ol hydrochlorideHCID 104510651-Chloro-4-((3-chloro-4-methoxybenzyl)amino)-6-phthalazinecarbonitrile

Produkt 1

HCID 698922484-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-[(3R)-3-hydroxypiperidino]phthalazine hydrochlorideAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 1.0 g 1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine, 1.92 g (R)-(+)-3-hydroxypiperidine hydrochloride, 1.80 g diisopropyl ethylamine and 12 ml 1-methyl-2-pyrrolidone was stirred at 170° C. for 1 hr and 15 min. After cooling, ethyl acetate was added to the reaction solution which was then washed with water and brine. It was dried over anhydrous sodium sulfate, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography. The resulting free compound was suspended in acetic acid/ethanol/water, 1 N aqueous hydrochloric acid was added thereto, and it was dissolved by heating. After cooling, the resulting crystals were collected by filtration to give 860 mg of the title compound as a yellow powder.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwas then washed with water and brine
  3. dry with materialIt was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography
  6. addition1 N aqueous hydrochloric acid was added
  7. dissolutionit was dissolved
  8. temperatureby heating
  9. temperatureAfter cooling
  10. filtrationthe resulting crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-68ff28ffad0a437f823f316ef44379ab
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699870B2

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