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-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxylate

HRID 501944Notes

Reaction equation

HRID 501944 reaction equation
[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:50]=[CH:51][CH:52]=[C:53]2[C:58]=1[NH:57][C:56](=[O:59])[N:55]([CH:60]1[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]1)[CH2:54]2.C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:48][C:49]1[CH:50]=[CH:51][CH:52]=[C:53]2[C:58]=1[NH:57][C:56](=[O:59])[N:55]([CH:60]1[CH2:65][CH2:64][N:63]([C:1]([O:2][C@H:3]([CH2:18][C:19]3[CH:27]=[C:26]([CH3:28])[C:25]4[C:21](=[CH:22][N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:35])([CH3:34])[CH3:36])[N:24]=4)[CH:20]=3)[C:4](=[O:17])[N:5]3[CH2:6][CH2:7][CH:8]([N:11]4[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]4)[CH2:9][CH2:10]3)=[O:37])[CH2:62][CH2:61]1)[CH2:54]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 211022172(1h)-Quinazolinone,8-fluoro-3,4-dihydro-3-(4-piperidinyl)-HCID 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 59424331(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-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3(4H)-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 8-fluoro-3-(piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-one (84.2 mg, 1.50 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 to give 78 mg (45%) as a colorless film. Mass spec.: 776.58 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography
  3. customto give 78 mg (45%) as a colorless film

Sources & evidence

ORD record
ord-ae869723878c410cb4c0efd0a779a33b
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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