5-FLUOROTHIAZOL-2-AMINE HYDROCHLORIDE synthesis
- Product Name:5-FLUOROTHIAZOL-2-AMINE HYDROCHLORIDE
- CAS Number:745053-64-9
- Molecular formula:C3H3FN2S.HCl
- Molecular Weight:154.59
40283-46-3
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Yield: 69%
Reaction Conditions:
Stage #1:2-aminothiazole-5-carboxylic acid with potassium phosphate in 1,4-dioxane;methanol;toluene at 20; for 2 h;
Stage #2: with 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate in 1,4-dioxane;methanol;toluene at 20; for 0.5 h;
Stage #3: with hydrogenchloride in 1,4-dioxane;methanol;tolueneProduct distribution / selectivity;
Steps:
1
2-Amino-thiazole-5-carboxylic acid (8.64 g, 60 mmol) and K3P04 (13.04 g, 90 mmol) were suspended in a mixture of methanol (100 ml), dioxane (150 ml) and toluene (150 ml). This was stirred at room temperature for 2 hours. Next, F-TEDA (34.5 g, 97 mmol) was added to the reaction vessel. This mixture was allowed to stir at room temperature for 30 minutes. After this period, the reaction mixture was filtered through a silica gel plug, acidified with HC1 in dioxane, concentrated in vacuo and lyophilized for 12 hours to afford the product, 5-Fluoro-thiazol-2-ylamine HC1 salt (6.42 g, 69%).
References:
TAKEDA SAN DIEGO, INC.;MATTSON, Matthew WO2011/115758, 2011, A1 Location in patent:Page/Page column 13-14
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