ANAGRELIDE
Anagrelide
CAS: 68475-42-3
Molecular Formula: C10H7Cl2N3O
ANAGRELIDE - Names and Identifiers
ANAGRELIDE - Physico-chemical Properties
| Molecular Formula | C10H7Cl2N3O |
| Molar Mass | 256.09 |
| Density | 1.77±0.1 g/cm3(Predicted) |
| Melting Point | 280 °C |
| Boling Point | 376.5°C at 760 mmHg |
| Flash Point | 181.5°C |
| Water Solubility | slightly soluble |
| Solubility | slightly soluble |
| Vapor Presure | 7.21E-06mmHg at 25°C |
| pKa | pKa 2.87 (H2O t=25 I=0.025) (Uncertain);10(H2O t=25 I=0.025) (Uncertain) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.79 |
ANAGRELIDE - Reference Information
| uses | platelet aggregation inhibitors for the treatment of various disorders associated with thrombocytosis. |
| production method | mmol concentrated nitric acid and 270mmol concentrated sulfuric acid were mixed and cooled to room temperature. 200mmol of 2, 3-dichlorotoluene was added to the reaction flask, and the mixed acid was added slowly under cooling in an ice bath. After addition, stir for about 10min. This was allowed to warm to room temperature and then to 50 °c and stirred for 3H at this temperature. The layers were separated by standing, the organic layer was separated, washed with water, and a 1% aqueous solution of sodium carbonate was added to neutralize the acidity. After extraction with ethyl acetate, the extract was washed with water, half-saturated brine, saturated brine, and then dried over anhydrous sodium sulfate. It was filtered and concentrated under reduced pressure. After separation by column chromatography, 2, 3-dichloro-6-nitrotoluene was obtained as a pale yellow solid in 50% yield. 24mmol of 2, 3-dichloro-6-nitrotoluene and 0.2mmol of crystalline benzoyl peroxide were dissolved in 6ml of anhydrous carbon tetrachloride, and 3.0mmol of bromine in carbon tetrachloride solution (solubility 0.5g/ml) was added, the light was irradiated with a halogen lamp in the reflux state. When the reaction solution changed from dark red to yellow-orange (about 3H) and the reactants were still present, another 3.0mmol of bromine was added and the reaction was continued for 3H. Excess bromine and solvent were removed under reduced pressure and purified by column chromatography, 2, 3-dichloro-6-nitrobenzyl bromide was obtained in a yield of 70%. 15mmol of 2, 3-dichloro-6-nitrobenzyl bromide was dissolved in 75ml of anhydrous Tetrahydrofuran, 17mmol of ethyl glycinate hydrochloride and 34mmol of anhydrous triethylamine were added under nitrogen, and the mixture was stirred for 14H. After filtration, the filtrate was concentrated under reduced pressure to give N-(2, 3-dichloro-6-nitrobenzyl) glycine ethyl ester hydrochloride in a yield of 99%. N-(2, 3-dichloro-6-nitrobenzyl) glycine ethyl ester hydrochloride was reduced with SnCl2/HCl to give N-(2, 3-dichloro-6-aminobenzyl) glycine ethyl ester. 0.28g of N-(2, 3-dichloro-6-aminobenzyl) glycine ethyl ester was dissolved in 2ml of isopropanol at room temperature with stirring, and 0.24g of N-cyanoimine diphenyl carbonate was added thereto, followed by stirring for 20min. The solid was filtered and washed with a small amount of benzene to give 0.23g of (2-cyanoimino-5, 6-dichloro-1, 2,3, Ethyl 4-tetrahydroquinazolin-3-yl) acetate, yield 70.6%. The crude product can be recrystallized from dimethylformamide with a melting point of 268-275 °c. At room temperature, 0.163G of the product obtained above was suspended in 2ml of acetic acid and stirred at 100 °c for 30min. After cooling, the precipitated crystals were filtered and washed with acetonitrile to give 300g of anagrelide with a melting point> 91% °c in a yield. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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