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| | tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Basic information | | Uses |
| Product Name: | tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate | | Synonyms: | tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate;tert-butyl 2-bromo-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)-carboxylate;tert-butyl 2-broMo-6;2-BroMo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylicacidtert-butylester;2-Bromo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine, N-BOC protected;Thiazolo[5,4-c]pyridine-5(4H)-carboxylic acid, 2-broMo-6,7-dihydro-, 1,1-diMethylethyl ester;tert-butyl 2-broMo-4H,5H,6H,7H-[1,3]thiazolo[5,4-
c]pyridine-5-carboxylate;5-Boc-2-bromo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine | | CAS: | 365996-06-1 | | MF: | C11H15BrN2O2S | | MW: | 319.22 | | EINECS: | | | Product Categories: | CHIRAL CHEMICALS;Heterocycle-Pyridine series | | Mol File: | 365996-06-1.mol | ![tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Structure](CAS/GIF/365996-06-1.gif) |
| | tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Chemical Properties |
| Melting point | 42-44 °C(Solv: ethyl ether (60-29-7)) | | Boiling point | 390.9±42.0 °C(Predicted) | | density | 1.495±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 1.23±0.20(Predicted) | | Appearance | White to off-white Solid | | InChI | InChI=1S/C11H15BrN2O2S/c1-11(2,3)16-10(15)14-5-4-7-8(6-14)17-9(12)13-7/h4-6H2,1-3H3 | | InChIKey | RXXKNZKFRAFFOH-UHFFFAOYSA-N | | SMILES | C1N(C(OC(C)(C)C)=O)CCC2N=C(Br)SC1=2 |
| Hazard Codes | T | | Risk Statements | 25 | | Safety Statements | 45 | | RIDADR | UN2811 | | HS Code | 2934100090 |
| | tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Usage And Synthesis |
| Uses | 2-Bromo-5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine is a reagent used for the synthesis of tetrahydrothiazolopyridines, which are potent antagonists for the smoothened (smo) receptor. | | Uses | 2-Bromo-5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine is a reagent used for the synthesis of tetrahydrothiazolopyridines, which are potent antagonists for the smoothened (smo) receptor. | | Synthesis | Method G - Step e: Synthesis of tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate
[0134] To a 100 mL DMF solution containing isoamyl nitrite (8.8 mL, 62.8 mmol) and copper(II) bromide (10.7 g, 48 mmol) was added tert-butyl 2-amino-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (10 g, 39.2 mmol) at 0°C. The reaction was carried out at 40°C and the reaction mixture was purified. The reaction mixture was stirred at 40°C for 30 min and then concentrated by evaporation. The concentrate was dissolved in 50 mL of water and extracted with dichloromethane (100 mL × 2). The organic phases were combined, washed with brine (30 mL × 2), and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (eluent: dichloromethane) afforded the target product tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (5.3 g, 42.4%) as a yellow solid. | | References | [1] Heterocycles, 2004, vol. 63, # 7, p. 1555 - 1561
[2] Patent: WO2014/113191, 2014, A1. Location in patent: Paragraph 0133; 0134
[3] Patent: US2013/144061, 2013, A1. Location in patent: Paragraph 0244; 0245; 0246; 0247
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 9, p. 3687 - 3706
[5] Patent: WO2018/13774, 2018, A1. Location in patent: Page/Page column 309 |
| | tert-butyl 2-bromo-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate Preparation Products And Raw materials |
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