2-Aminothiazole → HCID 800397, compound

To a solution of 2-(4-Chloro-phenoxy)-2-methyl-propionic acid (0.3 g, 1.4 mmol) in DCM (10 ml) was added triethylamine (0.23 ml, 1.68 mmol) and HOBt (0.23 g, 1.68 mmol) at 0° C. After stirring at this temperature for 5 min. added 2-aminothiazole (0.168 g, 1.68 mmol) and followed by EDCI (0.332 g, 1.68 mmol). The resulting solution was stirred for 12 h. then quenched with saturated aqueous NH4Cl solution (15 mL). The aqueous phase was extracted with CH2Cl2 (3×50 mL). The organic phase was successively washed with 2% HCl (50 mL), brine (50 mL) and dried over Na2SO4. After evaporation, the residue was purified by flash chromatography (1:10 ethyl acetate:hexanes) to give 2-(4-Chloro-phenoxy)-2-methyl-N-thiazol-2-yl-propionamide (0.325 g, 78%). 1H NMR (400 MHz, CDCl3): δ 1.58 (s, 6H), 6.76 (d, J=8.8 Hz, 2H), 7.01 (d, J=3.6 Hz, 1H), 7.18 (d, J=8.8 Hz, 2H), 7.50 (d, J=3.6 Hz, 1H), MS (EI) m/z 296.9 (M+1).

1. stirringThe resulting solution was stirred for 12 h.
2. customthen quenched with saturated aqueous NH4Cl solution (15 mL)
3. extractionThe aqueous phase was extracted with CH2Cl2 (3×50 mL)
4. washThe organic phase was successively washed with 2% HCl (50 mL), brine (50 mL)
5. dry with materialdried over Na2SO4
6. customAfter evaporation
7. customthe residue was purified by flash chromatography (1:10 ethyl acetate:hexanes)

ORD record

ord-77bc9002e57341b1a29f2a46fa59afe2

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940900B2