TERT-BUTYL 2-AMINO-6,7-DIHYDROTHIAZOLO[5,4-C]PYRIDINE-5(4H)-CARBOXYLATE Chemical Properties

Melting point:

91-94 °C

Boiling point:

412.8±45.0 °C(Predicted)

Density 

1.279±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Crystalline Powder

pka

5.23±0.20(Predicted)

color 

Off-white to brown

InChI

InChI=1S/C11H17N3O2S/c1-11(2,3)16-10(15)14-5-4-7-8(6-14)17-9(12)13-7/h4-6H2,1-3H3,(H2,12,13)

InChIKey

BMLHPGOMLGKYIJ-UHFFFAOYSA-N

SMILES

C1N(C(OC(C)(C)C)=O)CCC2N=C(N)SC1=2

Safety Information

HS Code 

2934100090

TERT-BUTYL 2-AMINO-6,7-DIHYDROTHIAZOLO[5,4-C]PYRIDINE-5(4H)-CARBOXYLATE Usage And Synthesis

Uses

2-Amino-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-5-carboxylic Acid tert-Butyl Ester is a reagent used in the synthesis of 2-(thiazol-2-amino)-4-arylaminopyrimidines, which are anaplastic lymphoma kinase (ALK) inhibitors.

Synthesis

To a 100 mL single-necked flask were added N-Boc-4-piperidone (10 g, 50 mmol), sulfur powder (3.22 g, 100 mmol), cyanamide (4.36 g, 100 mmol), and pyridine (40 mL). The reaction mixture was heated to 130 °C and kept for 90 min. After completion of the reaction, it was cooled to room temperature and the solid product was collected by filtration. The solid was washed with ethyl acetate and dried to give the dark brown solid product tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (9.7 g, 76% yield).

References

[1] Patent: CN105254613, 2016, A. Location in patent: Paragraph 0339; 0340; 0341
[2] European Journal of Medicinal Chemistry, 2017, vol. 139, p. 128 - 152
[3] Patent: WO2014/113191, 2014, A1. Location in patent: Paragraph 0124; 0125
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
[5] Heterocycles, 2004, vol. 63, # 7, p. 1555 - 1561

TERT-BUTYL 2-AMINO-6,7-DIHYDROTHIAZOLO[5,4-C]PYRIDINE-5(4H)-CARBOXYLATE(365996-05-0)Related Product Information

• tert-butyl 3-iodo-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate
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• TERT-BUTYL 6,7-DIHYDROTHIAZOLO[5,4-C]PYRIDINE-5(4H)-CARBOXYLATE
• 4,5,6,7-TETRAHYDRO-THIAZOLO[5,4-C]PYRIDIN-2-YLAMINE
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