2-Aminopyridine-4-boronic acid pinacol ester

• CAS: 1195995-72-2
• Catalog Number: ACM1195995722
• Category: Main Products
• Molecular Weight: 220.08
• Molecular Formula: C₁₁H₁₇BN₂O₂
• Synonyms: 2-AMINOPYRIDINE-4-BORONIC ACID PINACOL ESTER, 1195995-72-2, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine, 2-Amino-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, SureCN614168, MolPort-015-143-799, AKOS015947245, AB50841, OR17204, QC-4940, AK-41220, KB-20824, 2-Aminopyridine-4-boronic acid, pinacol ester, A-3769, (2-AMINOPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER, 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine, 4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDIN-2-YLAMINE
• IUPAC Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=NC=C2)N
• InChI Key: DCYKWKYBNWRLLZ-UHFFFAOYSA-N
• Exact Mass: 220.13800
• H-Bond Acceptor: 4
• H-Bond Donor: 1

Case Study

2-Aminopyridine-4-Boronic Acid Pinacol Ester Used in the Synthesis of DYRK1A Inhibitor

Lee Walmsley D, et al. Journal of medicinal chemistry, 2021, 64(13), 8971-8991.

This work used fragment- and structure-based discovery approaches to identify a highly selective, well-tolerated, brain-penetrant DYRK1A inhibitor that exhibited in vivo activity in tumor models. The lead molecule 34 in this pyrrolopyrimidine hit series inhibited DYRK1A and 1B with low nM potency and exhibited excellent selectivity over class 2 DYRKs. 2-Aminopyridine-4-boronic acid pinacol ester was one of the important raw materials in the synthesis of compound 34.
Synthesis procedures of compound 34
· The synthesis of compound 34 from 2-Aminopyridine-4-boronic acid pinacol ester involves several steps including coupling, purification, and functional group transformation.
· First, 2-aminopyridine-4-boronic acid pinacol ester and primary amines are combined in a mixture of THF and water under nitrogen. Potassium carbonate and a palladium catalyst are added, and the reaction mixture is heated at 60°C for 16 hours.
· The resulting mixture is then filtered, concentrated, and purified by flash column chromatography. The compound is collected as a colorless solid with a yield of 76%.
· In the next step, the compound is dissolved in THF and ethylenediamine is added, followed by TBAF. The reaction mixture is heated to 80°C for 14 hours. After cooling, the mixture is washed with water and brine, dried, and concentrated. The product is triturated and collected as a solid, which is dried under vacuum to yield the compound 34 as a colorless solid with a 59% yield.

Application of 2-Aminopyridine-4-Boronic Acid Pinacol Ester in the Synthesis of ROCK Inhibitors

Miao Z, et al. Bioorganic & medicinal chemistry letters, 2020, 30(6), 126966.

This work reports a series of thieno[2,3-d]pyrimidin-4(3H)-one derivatives as a new class of ROCK inhibitors. The hit compound 3-(3-methoxybenzyl)-7-(1H-indazol-5-yl)quinazolin-4(3H)-one (1) was structurally optimized to improve its potency. A total of 24 compounds (4a-c, 8a-l, 10a-e and 11a-e) were synthesized, of which the synthesis of 11a-e involved 2-Aminopyridine-4-boronic acid pinacol ester.
Structural optimization and synthesis of methoxybenzene
· Region Ⅲ of methoxy benzene was optimized while regions I and II were held constant as the optimal groups. Ten compounds (10a-e and 11a-e) were synthesized with varying substituted phenyl groups at region III.
· Based on the fragments present at region II, the compounds were divided into two categories: Group A (7-azaindole at region II) and Group B (2-aminopyridine in region II). The synthetic pathways for these compounds can be found in Scheme 3.
· Initial substitution reactions of 6 with different benzyl bromide substitutions yielded intermediates 9a-e. The final compounds 10a-e or 11a-e were obtained through Suzuki-Miyaura coupling of 9a-e with either 7-azaindole-4-boronic acid pinacol ester or 2-aminopyridine-4-boronic acid pinacol ester.
· The reactions were carried out under the following conditions: (i) DMF, K2CO3, room temperature, 12 hours, yielding 41%-53%; (ii) 1,4-dioxane/H2O (5/1), Pd(PPh3)4, K2CO3, N2, 95°C, 12 hours, resulting in 37%-55% yield.

Custom Q&A

What is the molecular formula of 2-Aminopyridine-4-boronic acid pinacol ester?

The molecular formula is C11H17BN2O2.

What are the synonyms of 2-Aminopyridine-4-boronic acid pinacol ester?

The synonyms are 1195995-72-2, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine, 2-AMINOPYRIDINE-4-BORONIC ACID PINACOL ESTER, 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine, (2-AMINOPYRIDIN-4-YL)BORONIC ACID PINACOL ESTER.

What is the computed IUPAC name of 2-Aminopyridine-4-boronic acid pinacol ester?

The computed IUPAC name is 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine.

What is the InChI of 2-Aminopyridine-4-boronic acid pinacol ester?

The InChI is InChI=1S/C11H17BN2O2/c1-10(2)11(3,4)16-12(15-10)8-5-6-14-9(13)7-8/h5-7H,1-4H3,(H2,13,14).

What is the InChIKey of 2-Aminopyridine-4-boronic acid pinacol ester?

The InChIKey is DCYKWKYBNWRLLZ-UHFFFAOYSA-N.

What is the canonical SMILES of 2-Aminopyridine-4-boronic acid pinacol ester?

The canonical SMILES is B1(OC(C(O1)(C)C)(C)C)C2=CC(=NC=C2)N.

What is the molecular weight of 2-Aminopyridine-4-boronic acid pinacol ester?

The molecular weight is 220.08 g/mol.

What is the CAS number of 2-Aminopyridine-4-boronic acid pinacol ester?

The CAS number is 1195995-72-2.

How many hydrogen bond donor counts does 2-Aminopyridine-4-boronic acid pinacol ester have?

It has 1 hydrogen bond donor count.

How many hydrogen bond acceptor counts does 2-Aminopyridine-4-boronic acid pinacol ester have?

It has 4 hydrogen bond acceptor counts.