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-hydroxy-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 501951Notes

Reaction equation

HRID 501951 reaction equation
[C:1](=[O:47])(OC1C=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.[OH:48][C:49]1([C:55]2[C:56](=[O:65])[NH:57][C:58]3[C:63]([CH:64]=2)=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[OH:48][C:49]1([C:55]2[C:56](=[O:65])[NH:57][C:58]3[C:63]([CH:64]=2)=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:54][CH2:53][N:52]([C:1]([O:2][C@H:3]([CH2:18][C:19]2[CH:27]=[C:26]([CH3:28])[C:25]3[C:21](=[CH:22][N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:34])[CH3:35])[N:24]=3)[CH:20]=2)[C:4](=[O:17])[N:5]2[CH2:6][CH2:7][CH:8]([N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:9][CH2:10]2)=[O:47])[CH2:51][CH2:50]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 594242883-(4-Hydroxypiperidin-4-yl)quinolin-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

Product 1

HCID 59424285(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-hydroxy-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 3-(4-hydroxypiperidin-4-yl)quinolin-2(1H)-one (55 mg, 1.0 equiv) in dimethylformamide (1 mL) was added diisopropylethylamine (79 μL, 0.45 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and purified by column chromatography (3:97:1 methanol/dichloromethane/triethylamine) to give 90 mg (52%) as a foam solid. Mass spec.: 771.48 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography (3:97:1 methanol/dichloromethane/triethylamine)
  3. customto give 90 mg (52%) as a foam solid

Sources & evidence

ORD record
ord-3146b738b2d6427380adb1fe27560857
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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