Thiazolo[5,4-c]pyridine-2-carboxylic acid, 4,5,6,7-tetrahydro-, ethyl ester, hydrochloride (1:1)

(Z)-Ethyl 5-( , N'-bis(tert-butoxycarbonyl)carbamimidoyl)-4, 5, 6, 7- tetrahydrothiazolo[5, 4-c]pyridine-2-carboxylate: 5-tert-Butyl 2-ethyl 6, 7- dihydrothiazolo[5, 4-c]pyridine-2, 5(4H)-dicarboxylate (0.500 g, 1.601 mmol) was treated with HC1 (4.0M in dioxane) (20.01 ml, 80 mmol) at room temperature. After 1 h, the precipitate was filtered, washed with Et20, and dried in vacuo. The amine hydrochloride salt was dissolved in DMF (10 mL) and treated with DIPEA (1.677 ml, 9.60 mmol) and (E)-tert-butyl (((tert-butoxycarbonyl)amino)( lH-pyrazol- 1 -yl)methylene)carbamate (0.497 g, 1.601 mmol). After 14 h, the reaction mixture was taken up in EtOAc (50 mL) and washed with water. The water layer was extracted with additional EtOAc. The combined organic layers were washed with 1.0M HQ solution, water, brine, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by column chromatography to give 1C (0.282 g, 38.8 % yield) as a white solid. MS (ESI) m/z: 455 (M+H)+.[00253] 1C. (Z)-Ethyl 5-( , N'-bis(tert-butoxycarbonyl)carbamimidoyl)-4, 5, 6, 7- tetrahydrothiazolo[5, 4-c]pyridine-2-carboxylate: 5-tert-Butyl 2-ethyl 6, 7- dihydrothiazolo[5, 4-c]pyridine-2, 5(4H)-dicarboxylate (0.500 g, 1.601 mmol) was treated with HC1 (4.0M in dioxane) (20.01 ml, 80 mmol) at room temperature. After 1 h, the precipitate was filtered, washed with Et20, and dried in vacuo. The amine hydrochloride salt was dissolved in DMF (10 mL) and treated with DIPEA (1.677 ml, 9.60 mmol) and (E)-tert-butyl (((tert-butoxycarbonyl)amino)( lH-pyrazol- 1 -yl)methylene)carbamate (0.497 g, 1.601 mmol). After 14 h, the reaction mixture was taken up in EtOAc (50 mL) and washed with water. The water layer was extracted with additional EtOAc. The combined organic layers were washed with 1.0M HQ solution, water, brine, dried over sodium sulfate, filtered, and concentrated. The crude material was purified by column chromatography to give 1C (0.282 g, 38.8 % yield) as a white solid. MS (ESI) m/z: 455 (M+H)+.

Molecular Weight:248.73
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:248.0386265
Monoisotopic Mass:248.0386265
Topological Polar Surface Area:79.5
Heavy Atom Count:15
Complexity:225
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes