ChemicalBook CAS DataBase List 5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride

5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride synthesis

8synthesis methods

Product Name:5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride
CAS Number:720720-96-7
Molecular formula:C8H11ClN2O2S
Molecular Weight:234.7

5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride can be used as a reagent for the synthesis of diamide derivatives (FXa inhibitors).

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1864-94-4 Synthesis

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5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride

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Yield:720720-96-7 86.5%

Reaction Conditions:

Stage #1:2-bromo-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine p-toluenesulfonate;phenyl formate with palladium diacetate;triethylamine;4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene in acetonitrile at 60; for 39 h;Autoclave;Inert atmosphere;
Stage #2: with lithium hydroxide monohydrate in tetrahydrofuran at 20; for 2 h;
Stage #3: with hydrogenchloride in methanol at 20; for 2 h;Cooling with ice;

Steps:

8 Example 8
5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride (1-c-hc1)
5-Methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylic acid hydrochloride (1-c-hc1)
To a 100 mL autoclave, compound (1-br-ts) (5.0 g, 12.34 mmol), Pd(OAc)₂ (2.8 mg, 0.0123 mmol), and xantphos (14.3 mg, 0.0247 mmol) were added.
In a glove box under a current of nitrogen, a solution containing phenyl formate (2.26 g, 18.50 mmol) and Et₃N (5.1 mL, 36.99 mmol) in degassed Me₃CN (20 mL:
the degassing was carried out by repeated reduction in pressure and purging with nitrogen three times) was added to the reaction mixture.
After sealing, the mixture was stirred at 60° C. for 39 hours.
After cooling of the reaction solution, toluene (50 mL) was added thereto, and the mixture was washed with 1% NaOH (50 mL) and 20% saline (25 mL) and concentrated into 10 mL under reduced pressure.
To the residue, THF (20 mL), H₂O (2 mL), and LiOH.H₂O (1.04 g, 2.0 equiv) were added, and the mixture was stirred at room temperature for 2 hours.
To the reaction solution, c-HCl (3.86 g, 3.5 eq.) and MeOH (50 mL) were added, and the slurry was stirred at room temperature for 1 hour and then under ice cooling for 1 hour and filtered.
The crystals obtained were washed with MeOH (10 mL) of 0 to 5° C. and dried under reduced pressure to obtain the title compound (2.51 g, 86.5%) as white crystals.
¹H-NMR (500 Hz, DMSO-d₆) δ: 4.63-4.55 (m, 2H), 3.62-3.57 (m, 2H), 3.23-3.14 (m, 2H), 2.94 (s, 3H).