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ChemicalBook CAS DataBase List Irinotecan hydrochloride trihydrate
136572-09-3

Irinotecan hydrochloride trihydrate synthesis

1synthesis methods
Irinotecan hydrochloride

100286-90-6

Irinotecan hydrochloride trihydrate

136572-09-3

(S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4';6,7]indolo[1,2-b]quinolin-9-yl[1,4'-bipiperidin]-1'-carboxylic acids were synthesized using (S)-4,11-diethyl-4-hydroxy-3,14-dioxo-3. 4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl [1,4'-bipiperidin]-1'-carboxylate trihydrate in the following general procedure: irinotecan hydrochloride (4.8 g), water (30 mL), ethanol (10 mL), and 5% hydrochloric acid solution (0.3 mL) were added to the reaction flask. The reaction mixture was heated to 75-80°C with continuous stirring until complete dissolution. Subsequently, the solution was cooled to 65°C and crystallization was induced by the addition of crystal seeds. The rate of cooling was controlled so that the solution was slowly cooled to 50 °C over 10 hours and then continued to 20 °C over the next 10 hours. Upon completion of crystallization, the solid product was collected by filtration and washed with pure water (16 mL). The resulting product was dried at room temperature and under atmospheric pressure to give 4.6 g of irinotecan hydrochloride trihydrate in 87% yield. The purity of the product was 99.9% by high performance liquid chromatography (HPLC). The structure of the product was confirmed by X-ray diffraction and infrared spectroscopy (IR) analysis to be consistent with form b as described in WO 03/074527. Microscopic observation showed that the average length of the crystals ranged from 50 μm to 200 μm.

100286-90-6 Synthesis
Irinotecan hydrochloride

100286-90-6
461 suppliers
$25.00/10mg

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Yield:136572-09-3 87%

Reaction Conditions:

with hydrogenchloride;water in ethanol at 75 - 80;

Steps:

3
Irinotecan HCl (4.8 g), water (30 ml), ethanol (10 ml) and 5 % HCl (0.3 ml) were charged. The mixture was heated to 75-80 °C and stirred until all dissolved. The solution was cooled to 65 0C and seed crystals were added. The solution was cooled in 10 hours to 50 °C and in 10 hours to 20 0C. The crystalline compound was filtered and washed with water ( 16 ml) .The product was dried under normal pressure at room temperature.The yield of irinotecan HCl 3H2O was 4.6 g (87 %).The HPLC-purity was 99.9 %. Based on X-ray and IR analysis the product is form b as defined in WO 03/074527. The average length of the crystals was 50 μm -200 μm by microscopic analysis.

References:

FERMION OY WO2006/84941, 2006, A2 Location in patent:Page/Page column 6

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