| Identification | Back Directory | [Name]
N-BOC-2-AMINO-5-BROMOTHIAZOLE | [CAS]
405939-39-1 | [Synonyms]
N-BOC-2-AMINO-5-BROMOTHIAZOLE
2-(Boc-aMino)-5-broMothiazole
N-Boc-2-Amino-5-bromothiazole95%
TERT-BUTYL 5-BROMOTHIAZOL-2-YLCARBAMATE
tert-butyl N-(5-bromothiazol-2-yl)carbamate
TERT-BUTYL (5-BROMO-1,3-THIAZOL-2-YL)CARBAMATE
tert-butyl N-(5-broMo-1,3-thiazol-2-yl)carbaMate
(5-BroMo-thiazol-2-yl)-carbaMic acid tert-butyl ester
2-amino-5-bromo-2H-thiazole-3-carboxylic acid tert-butyl ester
Carbamic acid, N-(5-bromo-2-thiazolyl)-, 1,1-dimethylethyl ester | [Molecular Formula]
C8H11BrN2O2S | [MDL Number]
MFCD07368614 | [MOL File]
405939-39-1.mol | [Molecular Weight]
279.15 |
| Chemical Properties | Back Directory | [Melting point ]
149 °C | [density ]
1.574±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
Solid | [pka]
4.58±0.70(Predicted) | [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 |
| Hazard Information | Back Directory | [Uses]
N-Boc-2-amino-5-bromothiazole is used as pharmaceutical intermediate. | [Synthesis]
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 |
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