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With sodium tetrahydroborate In methanol for 1 h; Cooling with ice
2-Amino-5-formylthiazole (11.5 g, 90 mmol) was dissolved in methanol (120 mL), and sodium borohydride (5.11 g, 135 mmol) was added thereto while cooling with ice, followed by stirring at the same temperature for 1 hour. Acetone (6 mL) and water (10 mL) were added to the reaction mixture, followed by stirring. The residue obtained by evaporating the reaction mixture under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:15), thereby giving the title compound (5.09 g, 43percent) as a white solid.
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2.25 h; Inert atmosphere; Reflux
[00363] A suspension of ethyl 2-amino-1,3-thiazole-5-carboxylate (1.72 g, 10 mmol) in anhydrous THF (100 mL) was cooled in an ice bath and treated with LiAIH4 (0.76 g, 20 mmol) portionwise, under nitrogen. The reaction mixture was warmed to room temperature and stirred for 90 minutes. After this time, additional LiAIH4 (0.76 g, 20 mmol) was added and thesuspension was heated to reflux for 45 minutes. After this time, the suspension was cooled in an ice bath and cautiously treated with ice chips, followed by concentrated aqueous ammonium hydroxide solution (10 mL) and stirred for 60 hours. The orange suspension was filtered through CeliteTM, washing with MeOH. The filtrate was evaporated under reduced pressure, adsorbed onto silica and purified by flash column chromatography, eluting with MeOH/DCM (5-10percent), with the desired fractions combined and concentrated under reduced pressure to afford the title compound (225 mg). LCMS method: Method 5, RT: 0.55 mm, Ml: 131 [M+1]
With methanol; sodium tetrahydroborate; at 0℃; for 3h;
At 0 C,Compound2-amino-5-Aldehydethiazole (12.0 g, 90 mmol) was dissolved in anhydrous methanol (250 mL), and sodium borohydride (10.0 g, 90 mmol) was slowly added and stirred for 3.0 h.The reaction was quenched by the addition of distilled water (20 mL).Dichloromethane extraction (50 mL × 3), anhydrous sodium sulfate (10 g), dried.Concentration gave 8.8 g of a yellow-brown solid.Yield: 72.7%.
43%
With sodium tetrahydroborate; In methanol; for 1h;Cooling with ice;
2-Amino-5-formylthiazole (11.5 g, 90 mmol) was dissolved in methanol (120 mL), and sodium borohydride (5.11 g, 135 mmol) was added thereto while cooling with ice, followed by stirring at the same temperature for 1 hour. Acetone (6 mL) and water (10 mL) were added to the reaction mixture, followed by stirring. The residue obtained by evaporating the reaction mixture under reduced pressure was purified using medium pressure silica gel flash column chromatography (methanol:chloroform=1:15), thereby giving the title compound (5.09 g, 43%) as a white solid.
EXAMPLE 2 Preparation of 2-amino-5-hydroxymethylthiazole: The epoxy propanal solution from example 1 is cooled to 0 C. With vigorous stirring, 76 g (1.00 mole) of thiourea was added in portions. After the addition is complete the water is removed under vacuum on a rotatory evaporator. A red-brown oil is isolated as the product (91.3 g).
With potassium carbonate; In acetonitrile; at 40℃; for 48h;
Example 46: {2-[({1-[(3,4-Dichlorophenyl)methyl]-1 H-1 ,2,3-triazol-4-yl}methyl)amino]- 1 ,3-thiazol-5-yl}methanolTo a solution of 4-(bromomethyl)-1-[(3,4-dichlorophenyl)methyl]-1 H-1 ,2,3-triazole (Intermediate 17) (0.21 g, 0.65 mmol) in acetonitrile was added (2-amino-1 ,3-thiazol-5- yl)methanol (0.175 g, 2 eq) followed by potassium carbonate (0.185 g, 2 eq) The reaction was stirred at 400C for 2 days. After evaporation, the residue was dissolved in ether and ethyl acetate and washed with water. The organic phase was dried over sodium sulphate, filtered and evaporated. The compound was purified by flash chromatography eluting with DCM/MeOH (92/8). The title compound was obtained as an <n="56"/>ochre powder (3 mg, 1.25%). HRMS calculated for Ci4H13CI2N5OS (M+H)+ 370.0296, found: 370.0297, Rt: 2.35 min. LC/MS: m/z 370 (M+H)+ Rt: 2.60 min.
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