Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 19171-19-8 | MDL No. : | MFCD12756407 |
Formula : | C13H11N3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UVSMNLNDYGZFPF-UHFFFAOYSA-N |
M.W : | 273.24 | Pubchem ID : | 134780 |
Synonyms : |
CC-4047;3-amino Thalidomide;Pomalidomide. Brand name: Pomalyst.
|
Chemical Name : | 4-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P501-P202-P201-P280-P308+P313-P405 | UN#: | N/A |
Hazard Statements: | H361 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | Example 14; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 14 was prepared similarly according to the procedure for Example 13 except that there was no acetic acid; the amount of triethylamine was reduced from 4.6 mol to 3.2 mol; and the refluxing time was increased from about 5 to 7 hours to about 47 hours. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 94percent. | |
92% | Example 15; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 15 was prepared similarly according to the procedure for Example 13 except that there was no acetic acid and the 4.6 mol of triethylamine was replaced with 9.2 mole of imidazole. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 92percent | |
85% | Example 16; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; Example 16 was prepared similarly according to the procedure for Example 13 except that the 4.6 mol of triethylamine was replaced with 9.2 mole of imidazole. The amount of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione in the reaction mixture was found to be 85percent. |
84% | Example 13; Preparation of 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione; According to Scheme E A mixture of <strong>[6946-22-1]<strong>[6946-22-1]3-aminophthalic acid</strong> hydrochloride</strong> (200 g, 0.92 mol, from Prosynth Ltd., Suffolk, UK), 3-aminoglutarimide hydrochloride (159 g, 0.96 mol, from Evotec OAI, Hamburg, Germany), acetonitrile (2.0 L), and acetic acid (577 g, 9.6 mol, from Fisher Scientifc) was charged into a reaction vessel. After the mixture was stirred for 15 minutes, triethylamine (465.0 g, 4.6 mol, from Aldrich, Milwaukee, Wis.) was added dropwise over 30-35 minutes while the reaction temperature was maintained at 20-25° C. Next, the reaction mixture was stirred further for 10-15 minutes and then refluxed at about 85 to 87° C. for about 5 to 7 hours or until the in-process control, i.e., HPLC AP at 240 nm, indicates that <2percent of the <strong>[6946-22-1]3-aminophthalic acid</strong> remained in the reaction mixture. After the reaction mixture was cooled to about 20 to 25° C. over 1-2 hours, 1.0 L of water was charged over 15-30 minutes at about 20 to 25° C. The resulting mixture was stirred at about 15 to 20° C. for about 20 to 30 minutes to provide a yellow solid precipitate, which was filtered, washed with DI water (3.x.1.0 L) and acetonitrile (2.x.500 mL), and then dried at about 35 to 40° C in vacuo to a constant weight at 210.0 g (84 percent). | |
68.5% | With acetic acid; triethylamine; In acetone; at 80 - 85℃; for 6h; | Acetonitrile (100 mL), acetic acid (26.28 mL, 459.5 mmol),Triethylamine (31.85 mL, 229.8 mmol), <strong>[6946-22-1]<strong>[6946-22-1]3-aminophthalic acid</strong> hydrochloride</strong> (10 g, 46.0 mmol),Aminopiperidine-2,6-dione hydrochloride (7.68 g, 46.6 mmol)Added to the reaction flask, heated to 80 ~ 85 ° C reflux, the reaction was complete after 6h,The reaction solution was cooled to 20 ~ 25 ° C, purified water was slowly added, the crystallization was stirred for 2h, filtered, the filter cake was dried under reduced pressure at 60 ± 5 ° C for 8h to obtain 8.6g black solid, yield 68.5percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.44% | With phenylsilane; dibutyltin chloride; In tetrahydrofuran; at 80℃; for 16h;Sealed tube; | To the stirred solution of 4-amino-2-(2,6-dioxo-3-piperidyl)isoindoline-l,3-dione 5-1 (100 00 mg, 365.97 umol) and lH-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> 5-2 (35.17 mg, 365.97 umol) in THF (3 mL) in a sealed tube were added phenylsilane (39.60 mg, 365.97 umol, 45.10 uL) and dibutyltin dichloride (133.44 mg, 439.17 umol, 98.12 uL). The reaction was heated at 80C for 16 hours and diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified by preparative TLC (2% methanol in dichloromethane) to afford 2-(2,6-dioxo-3-piperidyl)-4-(lH- pyrazol-4-ylmethylamino)isoindoline-l,3-dione (Compound 150) (51 mg, 144.34 umol, 39.44% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) d 12.75 (br, 1H), 11.08 (s, 1H), 7.70- 7 60 (br, i l l ). 7 58-7.54 (m, 2H), 7 15 (d, J = 8.56 Hz, i l l ). 7.03 (d, J = 7.08 Hz, 1 1 1 ), 6.79 (t, J = 5.84 Hz, 1H), 5.04 (dd, J = 12.76, 5.32 Hz, 1H), 4.38 (d, J = 5.60 Hz, 2H), 2.91-2.84 (m, 1H), 2.60-2.49 (m, 2H), 2.03-2.00 (m, 1H), LC MS: ES+ 354.05. |