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CAS No.: | 1032900-25-6 |
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Name: | Ceritinib (LDK378) |
Article Data: | 27 |
Molecular Structure: | |
Formula: | C28H36ClN5O3S |
Molecular Weight: | 558.145 |
Synonyms: | Ceritinib; LDK 378; 5-chloro-n4-(2-((1-methylethyl)sulfonyl)phenyl)-n2-(5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl)-2,4-pyrimidinediamine |
EINECS: | 811-457-8 |
Density: | 1.251±0.06 g/cm3(Predicted) |
Boiling Point: | 720.7±70.0 °C(Predicted) |
PSA: | 116.85000 |
LogP: | 7.26640 |
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
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With palladium on activated charcoal; hydrogen at 35℃; under 7500.75 Torr; | 97.9% |
4-(4-{5-chloro-4-[2-(propane-2-sulfonyl)phenylamino]pyrimidin-2-ylamino}-5-isopropoxy-2-methylphenyl)piperidine-1-carboxylic acid tert-butyl ester
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
With hydrogenchloride In ethyl acetate at 20℃; for 2h; | 97% |
With trifluoroacetic acid In tetrahydrofuran at 0 - 22℃; for 5h; Temperature; | 90.1% |
With trifluoroacetic acid at 20℃; for 1h; | 39% |
With trifluoroacetic acid In dichloromethane | |
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 2: sodium hydrogencarbonate / water; ethyl acetate View Scheme |
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
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With sodium hydroxide In water at 0 - 5℃; pH=8; | 96% |
With sodium hydroxide In ethanol; water; isopropyl alcohol at 55℃; Large scale; | 93% |
With sodium hydroxide In ethanol; water at 20 - 50℃; for 2h; Temperature; Inert atmosphere; | 90% |
2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-4-pyrimidinamine
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
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Stage #1: 2-chloro-N-(2-(isopropylsulfonyl)phenyl)-5-methyl-pyrimidin-4-amine; 5-chloro-N2-[2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl]-N4-[2-(isopropylsulfonyl)phenyl]pyrimidine-2,4-diamine dihydrochloride In isopropyl alcohol for 16h; Reflux; Large scale; Stage #2: With sodium hydroxide In ethanol; water; isopropyl alcohol at 55℃; Large scale; | 93% |
In ethanol; water; isopropyl alcohol for 16h; Reflux; Large scale; | 93% |
In 1,2-dimethoxyethane for 5h; Inert atmosphere; Reflux; | 74% |
2-isopropylsulfonylchlorobenzene
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
Stage #1: 2-isopropylsulfonylchlorobenzene; C24H34ClN5O3 With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate In toluene at 85 - 90℃; for 2h; Stage #2: With hydrogenchloride In ethanol; water at 45℃; for 1h; | 92.6% |
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
With trifluoroacetic acid In tetrahydrofuran at 8 - 30℃; for 5h; Temperature; | 91.3% |
1-bromo-2-(isopropylsulfonyl)benzene
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
Stage #1: 1-bromo-2-(isopropylsulfonyl)benzene; C24H34ClN5O3 With palladium diacetate; caesium carbonate; triphenylphosphine In tetrahydrofuran at 65 - 70℃; for 8h; Stage #2: With trifluoroacetic acid In dichloromethane at 25 - 30℃; for 3h; | 90.2% |
2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-4-pyrimidinamine
5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-((2-isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
Stage #1: 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-((2-isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine With hydrogenchloride In water; isopropyl alcohol at 25 - 30℃; for 1.5h; Buchwald-Hartwig Coupling; Stage #2: 2-chloro-N-(2-(isopropylsulfonyl)phenyl)-5-methyl-pyrimidin-4-amine In water; isopropyl alcohol for 44h; Reflux; | 75.4% |
With N-ethyl-N,N-diisopropylamine at 80℃; Inert atmosphere; | 2.5 g |
With toluene-4-sulfonic acid In isopropyl alcohol at 85℃; |
2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-4-pyrimidinamine
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
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Multi-step reaction with 2 steps 1: palladium diacetate; XPhos; caesium carbonate / tetrahydrofuran 2: trifluoroacetic acid / dichloromethane View Scheme | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; isopropyl alcohol / 75 - 77 °C / Large scale 2: sodium hydroxide / acetone; water / 20 - 55 °C / pH 12.0 View Scheme | |
Multi-step reaction with 3 steps 1: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / toluene / 0.33 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: sodium hydrogencarbonate / water; ethyl acetate View Scheme |
4-(4-amino-5-isopropoxy-2-methylphenyl)-piperidine-1-carboxylic acid tert-butyl ester
5-chloro-N2-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N4-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; XPhos; caesium carbonate / tetrahydrofuran 2: trifluoroacetic acid / dichloromethane View Scheme | |
Multi-step reaction with 3 steps 1: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / toluene / 0.33 h / 150 °C / Microwave irradiation 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: sodium hydrogencarbonate / water; ethyl acetate View Scheme | |
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C 2.1: isopropyl alcohol / 16 h / Reflux; Large scale 2.2: 55 °C / Large scale View Scheme |