Ammonia → HCID 86645973, compound

To a cooled mixture (0-5° C.) of (2R)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoic acid (1 g, 3.16 mmol) in CH2Cl2 (20 mL), 1,1-carbonyldiimidazole (CDI) (0.512 g, 3.16 mmol) was added. After stirring for 1 h at 0-5° C. gaseous ammonia was bubbled into the mixture for 4 h and then left stirring at room temperature until the complete disappearance of the starting material. The reaction was quenched adding a H3PO4/H2PO4− buffer solution (pH=2.0, 5 ml), the two phases were separated and the organic one washed with the same buffer (3×10 mL) and water (3×10 mL), dried over anhydrous Na2SO4 and evaporated under vacuum to give (2R)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl) propanamide (788 mg, 2.5 mmol) as a white solid (79%) used without further purification.

1. customwas bubbled into the mixture for 4 h
2. waitleft
3. customThe reaction was quenched
4. additionadding a H3PO4/H2PO4− buffer solution (pH=2.0, 5 ml)
5. customthe two phases were separated
6. washthe organic one washed with the same buffer (3×10 mL) and water (3×10 mL)
7. dry with materialdried over anhydrous Na2SO4
8. customevaporated under vacuum

ORD record

ord-aebfe6a14de546998dba0bcc4d26d2cc

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08133911B2