CAS No. 1227917-63-6, Ritlecitinib Intermediate

CAS No.:
1227917-63-6
Molecular Formula:
C11H22N2O2
Molecular weight (g/mol):
214.30
API Name:
Ritlecitinib
Last Drug Patent Expires:
12/3/2034 (Ritlecitinib)
Target:
JAK3

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Supply Chain

The Supply Chain Status in China

As of September 14, 2024, there are 41 potential suppliers manufacturing Ritlecitinib intermediate tert-butyl N-[(3R,6S)-6-methylpiperidin-3-yl]carbamate (CAS No. 1227917-63-6), including 26 factories, among which:

- The 25th percentile has an average registered capital of 1 million CNY;

- The 50th percentile has an average registerd capital of 2.44 million CNY;

- The 75th percentile has an average registered capital of 10 million CNY.

Feeling overwhelmed? Contact Unibest if you need us to quality-check other sources to strengthen your supply chain or to find a tailored solution for your specific procurement request.

Usage and ROS Analysis

Structure of Ritlecitinib

Ritlecitinib Structure

Three moieties can be identifed from Ritlecitinib structure:

Part A. The Adenine moiety, which is a common molecular building block for JAK inhibitor (read more about such magic bullet in drug development here)
Part B. The chiral moiety with two chiral centers; during API synthesis, the chiral purity of relevant intermediates is essential checkpoint for the cis conformation of Ritlecitinib API
Part C. The Acrylamide moiety

The Overall Synthesis of Ritlecitinib API

Ritlecitinib ROS

From the above Ritlecitinib synthesis map, an essential synthesis module is to form the Part B - cis chiral moiety, and the correct isomer can be conjugated with other two parts.

This Ritlecitinib intermediate, tert-butyl N-[(3R,6S)-6-methylpiperidin-3-yl]carbamate, CAS No. 1227917-63-6, contains two chrial centers and is the precursor of the essential Ritlecitinib intermediate (CAS No. 1207853-23-3) described in the Pfizer patents. It generated through racemic resolution using chiral acid (2R)-2-[(3,5-dinitrobenzoyl)amino]-2-phenylacetic acid (CAS No. 74927-72-3) with racemic CAS No. 1150618-39-5.

1227917-63-6

References

1. Wang, Z. et al. An alternative process for the synthesis of the key intermediate of ritlecitinib. Tetrahedron 101, 132503 (2021).

2. Hauske, J. R. Dopamine Transporter Inhibitors for Use in Treatment of Movement Disorders and Other Cns Indications. (2006).

3. Man, D. A. P. A. et al. 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors. (2013).

4. Liu, Y., Wan, W. & Li, X. Preparation method of optically pure 2-methylpiperidine-5-amine. (2023).

5. Holmes, I. et al. Compounds and Methods for the Treatment of Dermal and Ocular Disorders. (2023).

6. Kim, J. S. & Ahn, K. W. Manufacturing method of methylpiperidine amino pyrrolo pyrimidine. (2021).

7. 王仲清 et al. 一种pf-06651600中间体的制备方法. (2021).

8. Tao, Y. et al. Process Development and Scale Up of a Selective JAK3 Covalent Inhibitor PF-06651600. Org. Process Res. Dev. 23, 1872–1880 (2019).

9. Thorarensen, A. et al. Pyrrolo[2,3-D]pyrimidinyl, Pyrrolo[2,3-B]pyrazinyl and Pyr-Rolo[2,3-D]pyridinyl Acrylamides. (2015).

10. Critcher, D. J. et al. Pyrrolo[2,3-d]pyrimidine tosylate salt, crystalline form thereof and manufacturing process and intermediates thereto. (2020).