Diisopropylethylamine → (R)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(7-fluoro-2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxylate

HRID 501952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501952
[C:1](=O)([O:37]C1C=CC([N+]([O-])=O)=CC=1)[O:2][C@H:3]([CH2:18][C:19]1[CH:27]=[C:26]([CH3:28])[C:25]2[C:21](=[CH:22][N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:24]=2)[CH:20]=1)[C:4](=[O:17])[N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:7][CH2:6]1.[F:48][C:49]1[CH:58]=[C:57]2[C:52]([CH2:53][N:54]([CH:60]3[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]3)[C:55](=[O:59])[NH:56]2)=[CH:51][CH:50]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:48][C:49]1[CH:58]=[C:57]2[C:52]([CH2:53][N:54]([CH:60]3[CH2:65][CH2:64][N:63]([C:1]([O:2][C@H:3]([CH2:18][C:19]4[CH:27]=[C:26]([CH3:28])[C:25]5[C:21](=[CH:22][N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:35])([CH3:34])[CH3:36])[N:24]=5)[CH:20]=4)[C:4](=[O:17])[N:5]4[CH2:10][CH2:9][CH:8]([N:11]5[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]5)[CH2:7][CH2:6]4)=[O:37])[CH2:62][CH2:61]3)[C:55](=[O:59])[NH:56]2)=[CH:51][CH:50]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 594242967-fluoro-3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 59424375(R)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-nitrophenyl carbonate

Produkt 1

HCID 59424349(R)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(7-fluoro-2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (R)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-nitrophenyl carbonate (150 mg, 0.23 mmol) and 7-fluoro-3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (56.2 mg, 1.0 equiv) in dimethylformamide (1 mL) was added diisopropylethylamine (79 μL, 0.45 mmol) and the reaction stirred at room temperature overnight. The reaction was concentrated and purified by column chromatography (3:97:1 methanol/dichloromethane/triethylamine) to give 93 mg (53%) as a tan foam solid. Mass spec.: 776.48 (MH)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography (3:97:1 methanol/dichloromethane/triethylamine)
  3. customto give 93 mg (53%) as a tan foam solid

Quellen und Nachweise

ORD-Eintrag
ord-75954f159a3e49a798b4195ae60656e0
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772244B2

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