Benzyl isocyanate → HCID 178476645, Verbindung

HRID 897489

Reaktionsgleichung

Reaktionsgleichung von HRID 897489
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=2)=[CH:4][C:3]=1[O:31][CH3:32].[CH2:33]([N:40]=[C:41]=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>N1C=CC=CC=1>[C:3]([OH:31])(=[O:42])[CH3:4].[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@H:18]3[CH2:23][CH2:22][C@@H:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:41]([NH:40][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:42])=[C:3]([O:31][CH3:32])[CH:4]=3)[C:16]=12

Komponenten

4

Edukt 2

HCID 76639Benzyl isocyanateHCID 178488197HCID 178488197, Verbindung

Produkt 1

HCID 178476645HCID 178476645, VerbindungAusbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Cis-3-(4-amino-3-methoxyphenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.082 g, 0.000188 mol) was dissolved in anhydrous pyridine (1 mL), benzyl isocyanate (0.025 g, 0.000188 mol) was added and the resulting solution was stirred at ambient temperature for 20 hours. The solvent was removed under reduced pressure and the resulting residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield cis-N-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-N′-benzylurea acetate (0.009 g, 0.0000142 mol) as a white solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe resulting residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-53ccce89d1534b63b657a52be400c24a
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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