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2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile
  • 2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile

Model: 1187594-13-3
The compound is 2-(1-(Ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile, a fully assembled intermediate that incorporates four distinct pharmacophoric fragments into a single molecular scaffold in the baricitinib synthetic cascade. Structurally, the molecule comprises a 7H-pyrrolo[2,3-d]pyrimidine core (the heterocyclic skeleton common to multiple JAK inhibitors), a pyrazole spacer linking the core to a quaternary azetidine side chain, a ethylsulfonyl group at the azetidine nitrogen, and a terminal nitrile group appended to the azetidine ring. The 4-position of the pyrrolopyrimidine core bears the pyrazole substituent — the result of an earlier SNAr reaction with a pyrazole nucleophile — while the N-7 position remains protected by the acid-labile SEM (2-(trimethylsilyl)ethoxymethyl) group, allowing orthogonal deprotection at a late stage. The azetidine ring features a quaternary carbon bearing the acetonitrile side chain and the pyrazole linkage, a sterically congested architecture that is notably challenging to construct. The ethylsulfonyl group at the azetidine nitrogen persists through to the final API, where it contributes to baricitinib‘s JAK selectivity profile. The trimethylsilyl subunit embedded within the SEM group serves as a distinctive lipophilic handle that enhances solubility in organic media and facilitates chromatographic purification.

2-(1-(Ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile serves as a pivotal synthetic intermediate and pharmaceutical impurity in the industrial manufacturing process of baricitinib (Olumiant®), a selective and orally bioactive inhibitor of Janus kinase 1 (JAK1) and JAK2 approved by the FDA for the treatment of rheumatoid arthritis, atopic dermatitis, and alopecia areata. As a fully assembled advanced intermediate, 2-(1-(Ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile represents the penultimate stage before final SEM deprotection, and its efficient synthesis has been the subject of dedicated green chemistry and scale-up process development. In quality control contexts, 2-(1-(Ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile is officially recognized under multiple impurity designations — including Baricitinib Impurity 18, Baricitinib Impurity 6, and Baricitinib Impurity 29 — reflecting its status as a process-related substance that must be monitored and controlled in baricitinib drug substance during regulatory filing and commercial production. The compound‘s fully characterized structure and well-defined chemical properties make 2-(1-(Ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile an essential reference standard for analytical method development, method validation (AMV), quality control (QC) applications, Abbreviated New Drug Application (ANDA) filings, and commercial production of baricitinib.

2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile


Product Parameters

Parameter

Specification

CAS Number

1187594-13-3

Molecular Formula

C₂₂H₃₁N₇O₃SSi

Molecular Weight

501.68 g/mol

Purity

≥95% (reference standard grade); ≥98% (upon request)

Physical Form

Solid

Appearance

White to off-white to pale yellow solid

Boiling Point

696.8 ± 65.0 °C (Predicted)

Density

1.30 ± 0.1 g/cm³ (Predicted)

pKa

3.70 ± 0.30 (Predicted)

LogP

2.88 (Predicted)

Solubility

Soluble in DMSO, DMF, methanol, acetonitrile

Storage Condition

Sealed, 2–8°C, dry, protected from light, under inert atmosphere


Why Cosperpharm? – Our Competitive Advantages

Advantage

Detail

Production Strength

GMP-certified campus spanning 100+ mu, 3 multi-purpose workshops, 6 D-grade clean zone production lines, and 150+ reactors (20L–5000L), supporting high/low temp, anaerobic & hydrogenation; kg to ton scale production.

Fast Delivery

R&D samples: one week; commercial orders: 1–2 months after payment. Express (DHL/FedEx) or air/sea freight available.

Global Partners

Trusted by 30+ pharmaceutical companies in USA, Europe, India, Brazil, and Southeast Asia; long-term cooperation with generic drug manufacturers, CROs, and impurity standard distributors.

Licensed Exporter

Valid drug import/export license — no compliance delays.

Dual Quality Grades

Both research/pharma grade(≥98%)and high-purity impurity grade(≥99%)available to meet diverse customer needs.


Quality Assurance at Cosperpharm

Each batch undergoes:

● Gas chromatography (GC) – purity ≥97.0%

● Non‑aqueous titration – purity ≥97.0%

● Refractive index – confirmatory analysis

● ¹H NMR – structural verification

● Appearance – colorless to light yellow to light orange clear liquid

A comprehensive COA, MSDS (with full GHS information), and certificate of origin accompany every shipment.


FAQ

Q1: What are the multiple impurity designations for this compound?

A: This compound is recognized across the impurity landscape under several designations: Baricitinib Impurity 18, Baricitinib Impurity 6, Baricitinib Impurity 29, and Baricitinib Sulfonyl Impurity. One reference standard, multiple designation entries — allowing you to qualify once and use across multiple regulatory and QC contexts.

Q2: What is the shelf life of this reference standard?

A: Under recommended storage conditions (sealed, 2–8°C, dry, protected from light, under inert atmosphere), 2-(1-(Ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile has a shelf life of 2 years from the date of manufacture. Stability study data supporting this shelf life claim is available upon request.


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