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CAS No.: | 1223403-58-4 |
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Name: | LOXO-101 |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C21H22F2N6O2 |
Molecular Weight: | 428.441 |
Synonyms: | LOXO-101;(R)-N-(5-((S)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamide;(3S)-N-[5-[(2R)-2-(2,5-Difluorophenyl)-1-pyrrolidinyl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxy-1-pyrrolidinecarboxamide;ARRY 470;Larotrectinib |
Density: | 1.55±0.1 g/cm3(Predicted) |
Appearance: | White to yellow solid |
PSA: | 86.00000 |
LogP: | 3.02340 |
(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-amine
3-hydroxypyrrolidine
1,1'-carbonyldiimidazole
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Stage #1: 5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-amine; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 2h; Stage #2: 3-hydroxypyrrolidine In dichloromethane for 0.0833333h; | 91% |
3-hydroxypyrrolidine
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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With triethylamine In tetrahydrofuran at 75℃; for 6h; | 91% |
(R)-(+)-2-(2,5-difluorophenyl)pyrrolidine
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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With N-ethyl-N,N-diisopropylamine In ethanol at 30℃; | 85% |
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Multi-step reaction with 4 steps 1: ammonium chloride; iron / ethanol; water / Inert atmosphere; Reflux 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 10 °C 3: ethanol / 25 °C 4: N-ethyl-N,N-diisopropylamine / ethanol / 30 °C View Scheme | |
Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 5 h / 50 °C 2: acetic acid; hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / 7600.51 Torr 3: triethylamine / tetrahydrofuran / 1 h / 0 °C 4: triethylamine / tetrahydrofuran / 6 h / 75 °C View Scheme |
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 10 °C 2: ethanol / 25 °C 3: N-ethyl-N,N-diisopropylamine / ethanol / 30 °C View Scheme |
(R)-(+)-2-(2,5-difluorophenyl)pyrrolidine
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Multi-step reaction with 4 steps 1: triethylamine / tetrahydrofuran / 5 h / 50 °C 2: acetic acid; hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / 7600.51 Torr 3: triethylamine / tetrahydrofuran / 1 h / 0 °C 4: triethylamine / tetrahydrofuran / 6 h / 75 °C View Scheme |
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Multi-step reaction with 5 steps 1.1: triethylamine; p-toluenesulfonyl chloride / tetrahydrofuran / 12 h / 35 °C 1.2: 1 h 2.1: triethylamine / tetrahydrofuran / 5 h / 50 °C 3.1: acetic acid; hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / 7600.51 Torr 4.1: triethylamine / tetrahydrofuran / 1 h / 0 °C 5.1: triethylamine / tetrahydrofuran / 6 h / 75 °C View Scheme |
4H,5H-pyrazolo[1,5-a]pyrimidine-5-one
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Multi-step reaction with 6 steps 1: phosphorus trichloride / 6 h / 80 °C 2: nitric acid; sulfuric acid / 2 h / 0 - 5 °C 3: triethylamine / tetrahydrofuran / 5 h / 50 °C 4: acetic acid; hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / 7600.51 Torr 5: triethylamine / tetrahydrofuran / 1 h / 0 °C 6: triethylamine / tetrahydrofuran / 6 h / 75 °C View Scheme |
5-chloropyrazolo[1,5-a]pyrimidine
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Multi-step reaction with 5 steps 1: nitric acid; sulfuric acid / 2 h / 0 - 5 °C 2: triethylamine / tetrahydrofuran / 5 h / 50 °C 3: acetic acid; hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / 7600.51 Torr 4: triethylamine / tetrahydrofuran / 1 h / 0 °C 5: triethylamine / tetrahydrofuran / 6 h / 75 °C View Scheme |
(R)-5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)-3-nitropyrazolo[1,5-a]pyrimidine
(3S)-N-[5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidi n-3-yl]-3-hydroxypyrrolidine-1-carboxamide
Conditions | Yield |
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Multi-step reaction with 3 steps 1: acetic acid; hydrogen; palladium 10% on activated carbon / tetrahydrofuran / 2.5 h / 20 °C / 7600.51 Torr 2: triethylamine / tetrahydrofuran / 1 h / 0 °C 3: triethylamine / tetrahydrofuran / 6 h / 75 °C View Scheme |