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CAS No. : | 134272-64-3 | MDL No. : | MFCD09800491 |
Formula : | C6H9ClN2O2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | NJQOCRDPGFWEKA-UHFFFAOYSA-N |
M.W : | 176.60 | Pubchem ID : | 22118207 |
Synonyms : |
|
Chemical Name : | N-(2-Aminoethyl)maleimide Hydrochloride |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 |
---|---|---|
30.8% | With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; | To a solution of 4-azido-2-hydroxybenzoic acid N-hydroxysuccinimide ester (28 mg, 0.10 mmol) and N-(2-aminoethyl)maleimide hydrochloride (27 mg, 0.15 mmol) in DMF (250 muL) was added (i-Pr)2NEt (53 muL, 0.30 mmol) dropwise at 0 C. The reaction was allowed to warm room temperature, and stirred for 30 min. The reaction mixture was diluted with EtOAc, and then washed with 10% citric acid, H2O and brine. The organic layer was dried over Mg2SO4, and the solution was filtered, concentrated, and flash-chromatographed on silica gel to provide 1 (9.4 mg, 30.8%) as a pale yellow solid: mp >300 C; 1H NMR (CDCl3) delta 3.64 (m, 2H), 3.86 (t, J = 5.2 Hz , 2H) 6.53 (dd, J = 2.3 and 8.6 Hz, 1H) 6.62 (d, J = 2.3 Hz, 1H) 6.77 (s, 2H) 7.36 (d, J = 8.6 Hz, 1H); 13C NMR (CDCl3) delta 37.1, 39.9, 108.1, 110.1, 110.8, 127.2, 134.4, 146.0, 163.1, 169.8, 171.2. MS (ESI), calcd for C13H12N5O4 [M + H]+ 302.1, found 302.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reaction of commercially available Boc-Gly-Gly-Gly-OH (compound 8) with Nhydroxyxuccinimide and EDC coupling agent affords compound 9. Reaction of compound 9 with 1-(2-aminoethyl)-maleimide HC1 in the presence of a base such as diisopropyl ethyl amine (DIPEA) followed by Boc deprotection with HC1 in methoxymethyl ether gives compound 10. Reaction of compound 10 with glutamic anhydride gives compound 11. Reaction of compound 11 with DM? using EDC as coupling agent will give the desired product compound 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl acetamide; water; for 3h;Inert atmosphere; | A solution of 14.6 mM DM4 in DMA (2 mL, 29.2 mmol) was treated with 1:1 solution of saturated sodium bicarbonate to water (5%, 219 tl) followed by Sulfo-SPDB (29.7 mg, 0.073 mmol) under argon at room temperature with HPLC/MS monitoring. After 1 hour DM4 was consumed to give DM4-Sulfo-SPDB-DM4. Low Resolution MS calcd. (M1)= 1073.2; found (M-1)=1073.2.The reaction was treated with 1-(2-aminoethyl)-maleimide HC1 (12.90 mg, 0.073 mmol) under argon. After 3 hour desired product was formed. The material was purified on semi-prep HPLC C8 column using Water with 0.2% fomiic acid and 0.1% TEA and Acetonitrile. Low resolution MS, calcd. (M-1)=1098.34; found (M-1)=1098.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 0.25h; | (DM 1 -GMB- Ala-Gly-Gly)2-Lys-b-Ala-OH (5.3 mg, 0.0022 mmol) was dissolved in anhydrous dimethylformamide (0.25 mL) to which was added EDC (2.0 mg, 0.014 mmol). After 2 min 2-amino-ethyl-maleimide HC1 salt (1 mg, 0.0057 mmol) was added and the solution was stirred at room temperature for 15 min. The reaction mixture was purified by HPLC on a XB-C18 21.2x150 mm, 5muiotaeta column with a flow rate of 21.2mL/min. eluting with deionized water containing 0.1% formic acid using a gradient of acetonitrile 5% for 4 min then a linear gradient of 5% - 95% over 17 min. Fractions containing desired product were combined, frozen and lyophilized to give 2 mg (35 % yield) of white solid. MS [M + Na]+ calcd. 2537.0; found 2537.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; for 0.75h; | (SPDB-Ala-Gly-Gly)2-Lys-P-Ala-ONHS (22 mg, 0.020 mmol) was dissolved in anhydrous dimethyl formamide (400 mu) to which was added DM4 (30 mg, 0.038) with magnetic stirring. After 2 min deionized water (20 mu) was added then after 15 min diisopropylethyl amine (10 mu, mmol) and H2N-(CH2)2-Mal HC1 salt (3.7 mg, 0.022 mmol) were added. After an additional 30 min, sample was injected directly onto a 19 mm x 150 mm C18 HPLC column eluting with deionized water containing 0.2% formic acid with a 5-95% linear acetonitrile gradient. Flow rate was 20 mL/min. Fractions containing pure desired product were combined and frozen then lyophilized to give 19 mg (38% yield) of product as a white solid. MS [M + Na]+ calcd.2491.0; found 2491.3. |
A623105[ 125923-10-6 ]
1-(2-Aminoethyl)-1H-pyrrole-2,5-dione
Reason: Free-salt