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Ceritinib

Ceritinib structure

CAS No:
1032900-25-6
Formula:
C28H36ClN5O3S
Chemical Name:
Ceritinib
Synonyms:
2,4-Pyrimidinediamine,5-chloro-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-N2-[5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl]-;5-Chloro-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-N2-[5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl]-2,4-pyrimidinediamine;LDK 378;Ceritinib;Zykadia;1431456-10-8
Categories:
Biochemical Engineering > Inhibitors

Description

ChEBI: A member of the class of aminopyrimidines that is 2,6-diamino-5-chloropyrimidine in which the amino groups at positions 2 and 6 are respectively carrying 2-methoxy-4-(piperidin-4-yl)-5-methylphenyl and 2-(isopropylsulfonyl)phenyl substituents. Used for the treatment of ALK-positive metastatic non-small cell lung cancer.

Ceritinib Basic Attributes

Molecular Weight：

558.13514

Exact Mass：

558.14

EC Number：

-0

Characteristics

PSA：

114

XLogP3：

6.4

Density：

1.251±0.06 g/cm3(Predicted)

Boiling Point：

720.7±70.0 °C(Predicted)

Flash Point：

389.6±35.7 °C

Refractive Index：

1.595

Safety Information

Precautionary statement(s)：

P201, P202, P260, P264, P270, P273, P281, P308+P313, P314, P391, P405, P501

Hazard Statements：

H360

Ceritinib Use and Manufacturing

The intermediate P4 was dissolved in anhydrous DCM, EDCI and Hobt were added, and finally LDK378 was added, and the reaction was carried out at room temperature for 12 h.After the reaction was completed, water was added, extracted with EA three times, the organic layer was washed twice with saturated brine, dried over anhydrous sodium sulfate, concentrated, and the target product was separated by column chromatography with a yield of about 65%.Sebacic acid was used as a raw material (202 mg, 1 mmol), dissolved in 20 mL of DMF, and HATU (1140 mg, 3 mmol), DIPEA (774 mg, 6 mmol), LDK378 (279 mg, 0.5 mmol) were stirred at room temperature for 10 h.The reaction progress was monitored by TLC. After the reaction was completed, the reaction was quenched with 30 mL of water. After the aqueous layer was extracted with EA, the organic layers were combined, backwashed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then DCM / MeOH. Column chromatography was performed as the mobile phase. A white solid was obtained with a yield of about 53%.LDK378 was used as a raw material (330 mg, 0.6 mmol), dissolved in 50 mL of methanol, methyl acrylate (78 mg, 0.9 mmol) and triethylamine (240 mg, 2.4 mmol) were added, and the mixture was stirred at room temperature for 8 h.TLC measures the progress of the reaction.Treatment method: first remove the methanol by distillation under reduced pressure, add 150 mL of ethyl acetate, backwash the organic solution three times with water, remove the water with anhydrous sodium sulfate and concentrate under reduced pressure, and perform column chromatography with a PE / EA separation system to obtain a white solid.The yield is about 90%.Using LDK378 as a raw material (330mg, 0.6mmol), dissolved in 50mL methanol, Methyl acrylate (78 mg, 0.9 mmol) and triethylamine (240 mg, 2.4 mmol) were added, and the mixture was stirred at room temperature for 8 h. The progress of the reaction was monitored by TLC. Treatment method: first remove the methanol by distillation under reduced pressure, add 150 mL of ethyl acetate, backwash the organic solution three times with water, remove the water with anhydrous sodium sulfate and concentrate under reduced pressure, and perform column chromatography with a PE / EA separation system to obtain a white solid. The yield is about 90%.LDK378 was used as a raw material (330 mg, 0.6 mmol), dissolved in 50 mL of methanol, methyl acrylate (78 mg, 0.9 mmol), triethylamine (240 mg, 2.4 mmol) were added, and the mixture was stirred at room temperature for 8 h. The reaction progress was detected by TLC. Treatment method: first remove the methanol by distillation under reduced pressure, add 150 mL of ethyl acetate, backwash the organic solution three times with water, remove the water with anhydrous sodium sulfate, and concentrate under reduced pressure. Column chromatography using a PE / EA separation system to obtain a white solid. The yield is about 90%.

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