ChemicalBook CAS DataBase List 2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione

2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione synthesis

11synthesis methods

Product Name:2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione
CAS Number:446292-07-5
Molecular formula:C21H21N3O5
Molecular Weight:395.41

4-[4-(N-(3-chloro-(2R)-2-hydroxy-1-propyl)aMino)phenyl]Morpholin-3-one

1252018-10-2

1074-82-4

2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione

446292-07-5

Example 3: Preparation of (R)-2-(2-hydroxy-3-((4-(3-oxomorpholinyl)phenyl)amino)propyl)isoindoline-1,3-dione (7a): phthalimide potassium salt (7.16 g, 38.632 mmol) was added in a single addition to a mechanically stirred N,N-dimethylformamide (DMF, 60 mL) solution of 4-[4-(N-(3-chloro-2R-hydroxy-1-propyl)amino)phenyl]morpholine -3-one (10 g, 35.119 mmol) in a solution of N,N-dimethylformamide (DMF, 60 mL). After stirring the suspension at room temperature, it was heated to 100 °C and stirred continuously at this temperature for 3 hours. After the reaction was completed, the mixture was cooled to room temperature. Water (60 mL) was added and the suspension continued to be stirred for 15 minutes. Subsequently, the suspension was filtered through a Brinell funnel and the solid product was collected. The solid was washed with distilled water (2 x 40 mL) and dried under vacuum at 50 °C for 10 h to afford the target product (R)-2-(2-hydroxy-3-((4-(3-oxomorpholinyl)phenyl)amino)propyl)isoindoline-1,3-dione (12.55 g, 93% yield) as a white crystalline solid.1H NMR (400 MHz, DMSO-d6) δ. 2.99-3.05 (m, 1H), 3.14-3.2 (m, 1H), 3.59-3.69 (m, 4H), 3.91-3.94 (m, 2H), 3.97-4.05 (m, 1H), 4.14 (s, 2H), 5.16 (d, J = 5.2 Hz, 1H), 5.66 (t, J = 6.0 Hz, 1H), 6.61 (d, J = 6.0 Hz, 1H), 6.61 (d, J = 6.0 Hz, 1H). 6.61 (d, J = 8.7 Hz, 2H), 7.03 (d, J = 8.8 Hz, 2H), 7.82-7.88 (m, 4H).

161596-47-0 Synthesis

161596-47-0
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438056-69-0 Synthesis

438056-69-0
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446292-07-5
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Yield:446292-07-5 95%

Reaction Conditions:

in ethanol;water at 20; for 15 h;Solvent;Temperature;

Steps:

4-9 Example 4: Preparation of Compound C
Add 96g Compound A (made in accordance with the example of Patent Document CN100430384C, HPLC purity 96.0%), 960mL 95% (v/v) ethanol aqueous solution and 120g Compound B (made according to the method of Example 1) to the reaction flask, and reflux to react 15 hours, cooled to 20 °C, filtered, washed with 200 mL of 95% ethanol aqueous solution, and dried under vacuum at 70 ° C for 5 hours to obtain 188 g of compound C, off-white solid, molar yield: 95%, HPLC purity: 95.0%, impurity E content: 2.8 %, Ee value: 96.2%.

References:

Zhejiang Haixiang Pharmaceutical Co., Ltd.;Shanghai Haixiang Pharmaceutical Co., Ltd.;Tang Fanghui;Liang Chao;Ni Zhizhong;Zhao Fulu;Li Hongming CN111039937, 2020, A Location in patent:Paragraph 0066-0082

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1252018-10-2 Synthesis

1252018-10-2
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1074-82-4
501 suppliers
$5.00/25g

446292-07-5
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References