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Cas Database |
| Name |
Ruxolitinib |
EINECS | 1312995-182-4 |
| CAS No. | 941678-49-5 | Density | 1.40g/cm3 |
| PSA | 83.18000 | LogP | 3.46638 |
| Solubility | N/A | Melting Point |
N/A |
| Formula | C17H18N6 | Boiling Point | N/A |
| Molecular Weight | 306.37 | Flash Point | N/A |
| Transport Information | N/A | Appearance | N/A |
| Safety | Risk Codes | N/A | |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
Ruxolitinib; |
Article Data | 13 |
Ruxolitinib Synthetic route
- 1146629-80-2
(R)-(4-(1-(2-cyano-1-cyclopentylethyl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| With water; sodium hydroxide In methanol at 20℃; Product distribution / selectivity; | 100% |
| With sodium hydroxide; water In methanol at 20℃; for 15h; |
- 941685-40-1
(3R)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: (3R)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile With boron trifluoride diethyl etherate In acetonitrile at 60 - 70℃; for 5h; Stage #2: With ammonium hydroxide; water In acetonitrile at 20℃; for 12h; | 92.1% |
| Stage #1: (3R)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile With lithium tetrafluoroborate; water In acetonitrile Inert atmosphere; Reflux; Stage #2: With ammonia; water at 5 - 20℃; pH=9 - 10; Inert atmosphere; optical yield given as %ee; | 84% |
| With trifluoroacetic acid In dichloromethane for 6h; | 58% |
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| With trichlorophosphate In 1-methyl-pyrrolidin-2-one; dichloromethane at 20 - 30℃; for 3h; | 77.3% |
- 1146629-84-6
(3R)-3-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile
- 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 20 - 95℃; Product distribution / selectivity; Inert atmosphere; | 64.3% |
| With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 21h; Suzuki coupling; Inert atmosphere; | |
| With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 120℃; for 24h; Inert atmosphere; | 0.84 g |
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid; trifluoroacetic anhydride In toluene at 100℃; for 1h; | 61% |
- 941685-40-1
(3R)-3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile
A
- 941678-49-5
ruxolitinib
B
- 1236033-03-6
C18H20N6O
Conditions
| Conditions | Yield |
|---|---|
| With lithium tetrafluoroborate; water In acetonitrile Inert atmosphere; Reflux; | |
| With lithium tetrafluoroborate; water In acetonitrile at 12 - 80℃; |
- 1146629-83-5
(R)-3-(4-bromo-1H-pyrazol-1-yl)-3-cyclopentylpropanecarbonitrile
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 24 h / 20 - 90 °C / Inert atmosphere 2: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / 1,4-dioxane; water / 24 h / 120 °C / Inert atmosphere View Scheme | |
| Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -15 - 5 °C / Inert atmosphere 1.2: -5 - 5 °C / Inert atmosphere 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 50 - 60 °C / Inert atmosphere 3.1: hydrogenchloride / tetrahydrofuran; water / 20 °C / Reflux View Scheme |
- 1236033-03-6
C18H20N6O
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| With ammonia; water In acetonitrile at 0 - 20℃; Product distribution / selectivity; | n/a |
- 941685-27-4
4-(1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C 2: ethanol; hexane / Resolution of racemate 3: trifluoroacetic acid / dichloromethane / 6 h View Scheme | |
| Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C 2: Resolution of racemate 3: trifluoroacetic acid / dichloromethane / 6 h View Scheme | |
| Multi-step reaction with 4 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 26 h / 60 - 80 °C / Inert atmosphere 2: acetonitrile; tetrahydrofuran; acetone / 50 - 80 °C / Large scale 3: sodium hydroxide / ethyl acetate; water / 0 °C 4: lithium tetrafluoroborate / acetonitrile; water / 11 h / 0.8 - 27 °C View Scheme |
- 591769-05-0
3-cyclopentaneacrylonitrile
- 941678-49-5
ruxolitinib
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C 2: ethanol; hexane / Resolution of racemate 3: trifluoroacetic acid / dichloromethane / 6 h View Scheme | |
| Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 20 °C 2: Resolution of racemate 3: trifluoroacetic acid / dichloromethane / 6 h View Scheme | |
| Multi-step reaction with 4 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 26 h / 60 - 80 °C / Inert atmosphere 2: acetonitrile; tetrahydrofuran; acetone / 50 - 80 °C / Large scale 3: sodium hydroxide / ethyl acetate; water / 0 °C 4: lithium tetrafluoroborate / acetonitrile; water / 11 h / 0.8 - 27 °C View Scheme |
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