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

N-Boc-2-amino-5-bromothiazole Usage And Synthesis

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

N-Boc-2-amino-5-bromothiazole(405939-39-1)Related Product Information

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• 5-BROMO-2-TERT-BUTOXYCARBONYLAMINOTHIAZOLE-4-CARBOXYLIC ACID METHYL ESTER
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