N-Boc-2-amino-5-bromothiazole CAS 405939-39-1
N-Boc-2-amino-5-bromothiazole Basic information
| Product Name: | N-Boc-2-amino-5-bromothiazole |
| Synonyms: | TERT-BUTYL (5-BROMO-1,3-THIAZOL-2-YL)CARBAMATE;TERT-BUTYL 5-BROMOTHIAZOL-2-YLCARBAMATE;N-BOC-2-AMINO-5-BROMOTHIAZOLE;N-Boc-2-Amino-5-bromothiazole95%;tert-butyl N-(5-broMo-1,3-thiazol-2-yl)carbaMate;(5-BroMo-thiazol-2-yl)-carbaMic acid tert-butyl ester;2-(Boc-aMino)-5-broMothiazole;2-amino-5-bromo-2H-thiazole-3-carboxylic acid tert-butyl ester |
| CAS: | 405939-39-1 |
| MF: | C8H11BrN2O2S |
| MW: | 279.15 |
| EINECS: | |
| Product Categories: | Thiazole;API intermediates |
| Mol File: | 405939-39-1.mol |
N-Boc-2-amino-5-bromothiazole Chemical Properties
| Melting point | 149 °C |
| density | 1.574±0.06 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| pka | 4.58±0.70(Predicted) |
| form | Solid |
| Appearance | Off-white to yellow Solid |
| Water Solubility | Slightly soluble in water. |
| InChI | InChI=1S/C8H11BrN2O2S/c1-8(2,3)13-7(12)11-6-10-4-5(9)14-6/h4H,1-3H3,(H,10,11,12) |
| InChIKey | OIBKBVFFZYCBAQ-UHFFFAOYSA-N |
| SMILES | C(OC(C)(C)C)(=O)NC1=NC=C(Br)S1 |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22 |
| HS Code | 2933399990 |
| Uses | N-Boc-2-amino-5-bromothiazole is used as pharmaceutical intermediate. |
| Synthesis | 24424-99-5 61296-22-8 405939-39-1 General procedure for the synthesis of N-BOC-2-amino-5-bromothiazole from di-tert-butyl dicarbonate and 2-amino-5-bromothiazole hydrobromide: di-tert-butyl dicarbonate [(Boc)2O, 100.7 g, 0.461 mol, 1.2 eq.] was added to 900 mL of THF and 135 mL of pyridine (DMAP, 1.18 g, 9.7 mmol, 0.025 eq.) containing 2-amino-5-bromothiazole monohydrobromide (100 g, 0.385 mol, 1.0 eq.) and 4-(dimethylamino)pyridine (DMAP, 1.18 g, 9.7 mmol, 0.025 eq.) in a mixture of 900 mL THF and 135 mL Et3N. The reaction mixture was cooled to 0 °C using an ice bath. Subsequently, the reaction mixture was stirred at room temperature overnight, followed by vacuum concentration. The residue was stirred in EtOAc/heptane (1:10, 250 mL) at room temperature overnight and then filtered. The filtrate was washed with brine, dried, filtered, and concentrated in vacuo to afford the intermediate N-BOC-2-amino-5-bromothiazole as a yellow solid (91% yield). |
| References | [1] Synthesis, 2010, # 7, p. 1091 - 1096 [2] Patent: WO2018/112136, 2018, A1. Location in patent: Paragraph 00261 [3] Patent: US2009/36467, 2009, A1. Location in patent: Page/Page column 64; 72; 73 [4] Patent: US2012/108591, 2012, A1. Location in patent: Page/Page column 29 [5] Patent: WO2015/25172, 2015, A1. Location in patent: Page/Page column 118; 119 |
N-Boc-2-amino-5-bromothiazole Preparation Products And Raw materials
| Raw materials | Carbamic acid, 2-thiazolyl-, 1,1-dimethylethyl ester (9CI)-->2-Amino-5-bromothiazole-->Di-tert-butyl dicarbonate-->2-Amino-5-bromothiazole monohydrobromide-->4-Dimethylaminopyridine-->Triethylamine-->Tetrahydrofuran |
