ChemicalBook CAS DataBase List Ruxolitinib

Ruxolitinib synthesis

3synthesis methods

Product Name:Ruxolitinib
CAS Number:941678-49-5
Molecular formula:C17H18N6
Molecular Weight:306.37

Ruxolitinib, also known as INC424 and INCB18424 or INCB018424, is an orally bioavailable Janus-associated kinase (JAK) inhibitor with potential antineoplastic and immunomodulating activities. Ruxolitinib specifically binds to and inhibits protein tyrosine kinases JAK 1 and 2, which may lead to a reduction in inflammation and an inhibition of cellular proliferation. The JAK-STAT (signal transducer and activator of transcription) pathway plays a key role in the signaling of many cytokines and growth factors and is involved in cellular proliferation, growth, hematopoiesis, and the immune response; JAK kinases may be upregulated in inflammatory diseases, myeloproliferative disorders, and various malignancies.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

Lin, Qiyan; Meloni, David; Pan, Yongchun; Xia, Michael; Rodgers, James; Shepard, Stacey; Li, Mei; Galya, Laurine; Metcalf, Brian; Yue, Tai-Yuen; Liu, Pingli; Zhou, Jiacheng. Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-?Michael reaction. Jiacheng. Organic Letters. Volume 11. Issue 9. Pages 1999-2002. Journal. (2009).

1146629-80-2
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941678-49-5
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Yield:941678-49-5 100%

Reaction Conditions:

with water;sodium hydroxide in methanol at 20;Product distribution / selectivity;

Steps:

B

(3R)-Cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propionitrile ((R)-12, free base).; Method B.; To a stirred solution of (4-{1-[(1R)-2-cyano-1-cyclopentylethyl]-1H-pyrazol-4-yl}-7H-pyrrolo [2,3-d]pyrimidin-7-yl)methyl pivalate ((R)-21, 376 mg, 0.894 mmol) in methanol (4.0 mL, 99 mmol) at room temperature was added 1.0 M solution of sodium hydroxide in water (NaOH, 179 μL, 0.179 mmol, 2.0 equiv). The reaction mixture was stirred at room temperature for overnight (15 h). When LCMS showed the reaction was done cleanly, the reaction mixture was quenched with water (10 mL) and saturated aqueous NaCl solution (20 mL), and extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford (3R)-cyclopentyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propionitrile ((R)-12, free base, 274 mg, 274 mg theoretical, 100% yield) as a pale yellow foam, which was found to be identical as the material made from Method A.

References:

US2010/190981,2010,A1 Location in patent:Page/Page column 87-88

941685-40-1 Synthesis

1H-Pyrazole-1-propanenitrile, β-cyclopentyl-4-[7-[[2-(triMethylsilyl)ethoxy]Methyl]-7H-pyrrolo[2,3-d]pyriMidin-4-yl]-, (βR)-

941685-40-1
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941678-49-5
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$28.00/1mg

References

941685-40-1 Synthesis

941685-40-1
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941678-49-5
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1H-Pyrazole-1-propanenitrile, β-cyclopentyl-4-[7-(hydroxyMethyl)-7H-pyrrolo[2,3-d]pyriMidin-4-yl]-,(βR)-

1236033-03-6
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References

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