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Cas:1032900-25-6
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inquiryLIDE PHARMACEUTICALS LIMITED is a professional chemicals and APIs leading manufacturer in China. Our core business line covers APIs, Intermediates, Herb extract, etc. We are specialized in chemical synthesis, process development of pharmaceu
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inquiryJinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pu
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inquiryCeritinib CAS No.: 1032900-25-6 Name: Ceritinib Synonyms: 5-Chloro-N4-[2-[(1-methylethyl)sulfonyl]phenyl]-N2-[5-methyl-2-(1-methylethoxy)-4-(4-piperidinyl)phenyl]-2,4-pyrimidinediamine
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inquiryhigh quality Appearance:White or off-white Solid Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea Port:shanghai
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inquirychengdu and import and export trade co., LTD., who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do res
Ceritinib (LDK378) CAS:1032900-25-6 Chinese alias: Seretini English Name: ceritinib English alias: CS-1406; LDK378 Ceritinib; 5-chloro-N2-(2-isopropoxy-5-methyl-4-piperidin-4-piperiperidin-4-piperiperidin-4-piperiperidin-4-yl phenyl) -N
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inquiryStock products, own laboratory Appearance:White to Off-White solid Storage:-20°C Freezer Package:Grams, Kilograms Application:For R&D Transportation:According to customer request Port:shanghai
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Cas:1032900-25-6
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inquiryWith our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin
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inquiryProduct name Ceritinib CAS NO. 1032900-25-6 Synonyms Ceritinib Category Pharmaceutical Raw Materials,Active Pharmaceutical Ingredients,Bulk Drugs,Fine Chemicals.
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Cas:1032900-25-6
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inquiryHanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr
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inquiryCeritinib (LDK378) CAS:1032900-25-6 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic inte
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inquiry1. "Top 100 innovation-oriented export enterprises Of Hangzhou" honored by Hangzhou government 2. Specialized in the fine chemicals and pharmaceuticals 3. A leading manufacturer and trader of
Cas:1032900-25-6
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inquiry5-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 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 |
---|---|
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 |
---|---|
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 |
---|---|
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 |
1-amino-2-(isopropylsulphonyl)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 |
---|---|
Multi-step reaction with 4 steps 1.1: chloroform / 6 h / 60 °C 2.1: acetonitrile / 8 h / 80 °C 3.1: hydrogen; 0.5% Pd/C / methanol / 8 h / 20 °C / 760.05 Torr 4.1: nitrous acid isobutyl ester / acetone / 2 h / 10 °C 4.2: 1 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl acetamide / 1 h / 0 °C 1.2: 2 h / 20 - 25 °C 2.1: toluene-4-sulfonic acid / isopropyl alcohol; water / 24 h / 140 °C / Autoclave View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; dimethyl sulfoxide / 0.5 h / 0 °C 1.2: 15 h / 0 - 20 °C 2.1: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / toluene / 0.33 h / 150 °C / Microwave irradiation 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4.1: 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 |
---|---|
Multi-step reaction with 3 steps 1.1: acetonitrile / 8 h / 80 °C 2.1: hydrogen; 0.5% Pd/C / methanol / 8 h / 20 °C / 760.05 Torr 3.1: nitrous acid isobutyl ester / acetone / 2 h / 10 °C 3.2: 1 h / 80 °C 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 |
---|---|
Stage #1: C33H46N6O5S With nitrous acid isobutyl ester In acetone at 10℃; for 2h; Sandmeyer Reaction; Stage #2: With hydrogenchloride In water at 80℃; for 1h; Sandmeyer Reaction; |
2,5-dichloro-N-[2-[(1-methylethyl)sulfonyl]phenyl]-4-pyrimidinamine
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: boron trifluoride / isopropyl alcohol / 10 h / 65 °C 2: trifluoroacetic acid / tetrahydrofuran / 5 h / 0 - 22 °C 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 |
---|---|
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 2 steps 1: isopropyl alcohol / Reflux 2: sodium hydroxide / water; acetone / 55 °C View Scheme |
2-aminophenyl isopropyl sulphide
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 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / Reflux; Large scale 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 15 °C / Large scale 3: isopropyl alcohol / 24 h / Reflux; Large scale View Scheme | |
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 24 h / 8 °C / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 2 - 25 °C / Inert atmosphere 3.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 25 - 30 °C 3.2: 44 h / Reflux View Scheme |
ortho-nitrofluorobenzene
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 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 80 - 90 °C / Large scale 2.1: pyrographite / ethyl acetate / 30 - 40 °C / Large scale 2.2: 1216.08 Torr / Large scale 3.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / Reflux; Large scale 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 15 °C / Large scale 5.1: isopropyl alcohol / 24 h / Reflux; Large scale View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 25 °C 3.1: hydrogen; palladium on activated charcoal / methanol / 6 h / 3102.97 Torr 4.1: sodium hydride / N,N-dimethyl acetamide / 1 h / 0 °C 4.2: 2 h / 20 - 25 °C 5.1: toluene-4-sulfonic acid / isopropyl alcohol; water / 24 h / 140 °C / Autoclave View Scheme | |
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 100 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 760.05 Torr 4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Cooling with ice 4.2: 16 h / 20 °C 5.1: palladium diacetate; caesium carbonate / tetrahydrofuran / 2 h / Reflux 6.1: trifluoroacetic acid / 1 h / 20 °C View Scheme |
2-(isopropyl sulfanyl)nitrobenzene
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 4 steps 1.1: pyrographite / ethyl acetate / 30 - 40 °C / Large scale 1.2: 1216.08 Torr / Large scale 2.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / Reflux; Large scale 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 15 °C / Large scale 4.1: isopropyl alcohol / 24 h / Reflux; Large scale View Scheme | |
Multi-step reaction with 4 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 25 °C 2.1: hydrogen; palladium on activated charcoal / methanol / 6 h / 3102.97 Torr 3.1: sodium hydride / N,N-dimethyl acetamide / 1 h / 0 °C 3.2: 2 h / 20 - 25 °C 4.1: toluene-4-sulfonic acid / isopropyl alcohol; water / 24 h / 140 °C / Autoclave View Scheme | |
Multi-step reaction with 5 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / methanol / 6 h / 760.05 Torr 3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Cooling with ice 3.2: 16 h / 20 °C 4.1: palladium diacetate; caesium carbonate / tetrahydrofuran / 2 h / Reflux 5.1: trifluoroacetic acid / 1 h / 20 °C 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 |
---|---|
Multi-step reaction with 2 steps 1: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 100 °C 2: palladium on activated charcoal; hydrogen / 35 °C / 7500.75 Torr View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride / water; isopropyl alcohol / pH 1 2: hydrogen / methanol / 8 h / 90 °C / 7500.75 Torr 3: isopropyl alcohol / Reflux 4: sodium hydroxide / water; acetone / 55 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride / isopropyl alcohol / pH 1 2.1: palladium on activated charcoal; hydrogen / methanol / 8 h / 90 °C / 7500.75 Torr 2.2: Cooling with ice 3.1: isopropyl alcohol / Reflux 4.1: sodium hydroxide / water; acetone / 55 °C View Scheme |
4-(5-isopropyloxy-2-methyl-4-nitrophenyl)pyridine
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 5 steps 1: acetone / Reflux 2: sodium tetrahydroborate / tetrahydrofuran / 5 °C / Inert atmosphere 3: iron(III) chloride; pyrographite; hydrazine hydrate / ethanol / Reflux 4: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 100 °C 5: palladium on activated charcoal; hydrogen / 35 °C / 7500.75 Torr View Scheme | |
Multi-step reaction with 5 steps 1: ethyl acetate 2: sodium tetrahydroborate / tetrahydrofuran / 5 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C 4: hydrogenchloride / ethyl acetate 5: 1,2-dimethoxyethane / 130 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: hydrogenchloride / ethyl acetate 2: sodium tetrahydroborate / tetrahydrofuran / 5 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C 4: hydrogenchloride / ethyl acetate 5: 1,2-dimethoxyethane / 130 °C / Inert atmosphere 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 |
---|---|
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran / 5 °C / Inert atmosphere 2: iron(III) chloride; pyrographite; hydrazine hydrate / ethanol / Reflux 3: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 100 °C 4: palladium on activated charcoal; hydrogen / 35 °C / 7500.75 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate / ethanol / 16 h / 20 - 25 °C 2.1: palladium; hydrogen / methanol / 6 h / 50 °C / 2660.18 Torr 3.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 25 - 30 °C 3.2: 44 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1: sodium tetrahydroborate; hydrogenchloride / methanol; water 2: hydrogenchloride / water; isopropyl alcohol / pH 1 3: hydrogen / methanol / 8 h / 90 °C / 7500.75 Torr 4: isopropyl alcohol / Reflux 5: sodium hydroxide / water; acetone / 55 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; hydrogenchloride; methanol / water / Cooling 2.1: hydrogenchloride / isopropyl alcohol / pH 1 3.1: palladium on activated charcoal; hydrogen / methanol / 8 h / 90 °C / 7500.75 Torr 3.2: Cooling with ice 4.1: isopropyl alcohol / Reflux 5.1: sodium hydroxide / water; acetone / 55 °C 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 |
---|---|
Multi-step reaction with 3 steps 1: iron(III) chloride; pyrographite; hydrazine hydrate / ethanol / Reflux 2: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / tetrahydrofuran / 100 °C 3: palladium on activated charcoal; hydrogen / 35 °C / 7500.75 Torr View Scheme | |
Multi-step reaction with 3 steps 1: hydrogen; 50% palladium on charcoal / methanol / 72 h / 4137.29 Torr 2: hydrogenchloride / methanol / 0.17 h / 0 °C 3: toluene-4-sulfonic acid / isopropyl alcohol; water / 24 h / 140 °C / Autoclave View Scheme | |
Multi-step reaction with 2 steps 1.1: palladium; hydrogen / methanol / 6 h / 50 °C / 2660.18 Torr 2.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 25 - 30 °C 2.2: 44 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogen; palladium on activated charcoal / methanol / 25 - 30 °C / 3102.97 Torr 1.2: 0 - 50 °C 2.1: isopropyl alcohol / 20 h / Inert atmosphere; Reflux 2.2: 55 - 60 °C / pH 9.7 View Scheme | |
Multi-step reaction with 3 steps 1.1: platinum(IV) oxide; hydrogen / methanol / 25 - 30 °C / 3102.97 Torr 2.1: hydrogen; 5%-palladium/activated carbon / methanol / 25 - 30 °C / 3361.55 Torr 2.2: 25 - 30 °C / pH 1.6 3.1: isopropyl alcohol / 20 h / Inert atmosphere; Reflux 3.2: 55 - 60 °C / pH 9.7 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 |
---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C 2: hydrogenchloride / ethyl acetate 3: 1,2-dimethoxyethane / 130 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 20 °C / 7500.75 Torr 2: hydrogenchloride / ethyl acetate 3: 1,2-dimethoxyethane / 5 h / Inert atmosphere; Reflux 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 |
---|---|
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran / 5 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C 3: hydrogenchloride / ethyl acetate 4: 1,2-dimethoxyethane / 130 °C / Inert atmosphere 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 |
---|---|
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / tetrahydrofuran / 5 °C / Inert atmosphere 2: palladium on activated charcoal; hydrogen / tetrahydrofuran / 20 °C 3: hydrogenchloride / ethyl acetate 4: 1,2-dimethoxyethane / 130 °C / Inert atmosphere View Scheme |
1-chloro-2-methyl-4-nitro-5-(propan-2-yloxy)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 |
---|---|
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 5 h / 120 °C / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / methanol; water / 20 °C 3: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / N,N-dimethyl-formamide / 10 h / 120 °C / Inert atmosphere 4: hydrogenchloride / ethyl acetate / 2 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate / 1,4-dioxane / 48 h / 100 °C 2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 48 h / 20 °C 3: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / toluene / 0.33 h / 150 °C / Microwave irradiation 4: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5: sodium hydrogencarbonate / water; ethyl acetate View Scheme | |
Multi-step reaction with 7 steps 1: potassium carbonate; palladium diacetate; triphenylphosphine / 1,4-dioxane / 24 h / Reflux; Inert atmosphere 2: tetrahydrofuran / Reflux 3: sodium tetrahydroborate; hydrogenchloride / methanol; water 4: hydrogenchloride / water; isopropyl alcohol / pH 1 5: hydrogen / methanol / 8 h / 90 °C / 7500.75 Torr 6: isopropyl alcohol / Reflux 7: sodium hydroxide / water; acetone / 55 °C View Scheme |
tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate
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 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 5 h / 120 °C / Inert atmosphere 2: 5%-palladium/activated carbon; hydrogen / methanol; water / 20 °C 3: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / N,N-dimethyl-formamide / 10 h / 120 °C / Inert atmosphere 4: hydrogenchloride / ethyl acetate / 2 h / 20 °C View Scheme |
4-(2-methyl-4-nitro-5-isopropoxyphenyl)-5,6-dihydropyridine-1(2H)-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 3 steps 1: 5%-palladium/activated carbon; hydrogen / methanol; water / 20 °C 2: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / N,N-dimethyl-formamide / 10 h / 120 °C / Inert atmosphere 3: hydrogenchloride / ethyl acetate / 2 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 48 h / 20 °C 2: bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate / toluene / 0.33 h / 150 °C / Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4: 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 |
---|---|
Multi-step reaction with 4 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos; toluene-4-sulfonic acid hydrazide; lithium tert-butoxide / 1,4-dioxane / 0.08 h / Inert atmosphere 1.2: 16 h / 110 °C / Inert atmosphere 2.1: hydrogen; palladium on activated charcoal / methanol / 72 h / 4137.29 Torr 3.1: hydrogenchloride / methanol / 0.17 h / 0 °C 4.1: toluene-4-sulfonic acid / isopropyl alcohol; water / 24 h / 140 °C / Autoclave View Scheme | |
Multi-step reaction with 5 steps 1: TurboGrignard / tetrahydrofuran / 6.1 h / Inert atmosphere; Reflux 2: toluene-4-sulfonic acid / toluene / Reflux 3: hydrogen; palladium on activated charcoal / methanol / 72 h / 4137.29 Torr 4: hydrogenchloride / methanol / 0.17 h / 0 °C 5: toluene-4-sulfonic acid / isopropyl alcohol; water / 24 h / 140 °C / Autoclave 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 |
---|---|
Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / methanol / 72 h / 4137.29 Torr 2: hydrogenchloride / methanol / 0.17 h / 0 °C 3: toluene-4-sulfonic acid / isopropyl alcohol; water / 24 h / 140 °C / Autoclave 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
dibenzyl phosphochloridate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 24h; | 96% |
pentyl chloroformate
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 dmap In dichloromethane at 20℃; | 96% |
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
chlorophosphoric acid diphenyl ester
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 24h; | 95% |
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
methyl chloroformate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; | 95% |
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
isobutyl chloroformate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; | 95% |
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
acrylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 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; acrylic acid methyl ester With triethylamine at 20℃; for 8h; Michael Addition; Stage #2: With sodium hydroxide In methanol; water at 20℃; for 8h; Stage #3: With hydrogenchloride In water pH=2; | 95% |
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
chloroformic acid ethyl ester
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; | 94% |
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
diethyl chlorophosphate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 24h; | 90% |
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
acrylic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 8h; | 90% |
With triethylamine In methanol at 20℃; for 8h; | 90% |
With triethylamine In methanol at 20℃; for 8h; | 90% |
With triethylamine In methanol at 20℃; for 8h; | 90% |
2-hydroxyethyl 4-methylbenzenesulfonate
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
2-[4-(4-{5-chloro-4-[2-(propane-2-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-2-methyl-phenyl)-piperidin-1-yl]-ethanol
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 85℃; | 88% |
bromoacetic 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 potassium carbonate In acetonitrile for 5h; Reflux; | 76% |
With potassium carbonate In acetonitrile for 5h; Reflux; | 76% |
With potassium carbonate In acetonitrile for 5h; Reflux; | 76% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 75% |
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
[(18)F]-2-fluoroethyltosylate
Conditions | Yield |
---|---|
In acetonitrile for 0.333333h; Heating; | 74% |
fluorescein isothiocyanate
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 N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 40℃; for 1h; Darkness; | 72% |
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 N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 6h; | 68% |
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
1-azido-4-iodobutane
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 16h; | 66% |
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 benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; | 65% |
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
2-fluoroethyl tosylate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 85℃; for 4h; | 64% |
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
carbonochloridic acid, chloromethyl ester
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0 - 20℃; | 63% |
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
2-((E)-2-((E)-2-((3-(4-(4-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-5-isopropoxy-2-methylphenyl)piperidin-1-yl)-3-oxopropyl)thio)-3-(2-((E)-3,3-dimethyl-5-sulfo-1-(3-sulfopropyl)indolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-3,3-dimethyl-1-(3-sulfopropyl)-3H-indole-5-sulfonic acid
Conditions | Yield |
---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 40℃; for 2h; Darkness; | 62% |
1,10-decanedioic acid
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 N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 10h; | 53% |
[(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl)amino]acetic acid
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 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dimethyl sulfoxide at 20℃; | 52% |
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