Triethylamine → N-Methoxy-N-methyl-1,3-thiazole-5-carboxamide

Triethylamine (2.77 mL, 19.9 mmol) was added slowly to a mixture of commercially available thiazole-5-carboxylic acid (1.03 g, 7.98 mmol), N,O-dimethylhydroxylamine hydrochloride (0.778 g, 7.98 mmol), and EDCI (1.83 g, 9.57 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 72 hours then quenched with saturated aqueous NaHCO3. Water (50 mL) was added followed by additional CH2Cl2. The mixture was stirred for 10 minutes and layers were separated. The CH2Cl2 layer was dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the residual oil was chromatographed (CH2Cl2/EtOAc) to provide the title compound as a white solid.

1. customthen quenched with saturated aqueous NaHCO3
2. additionWater (50 mL) was added
3. stirringThe mixture was stirred for 10 minutes
4. customlayers were separated
5. dry with materialThe CH2Cl2 layer was dried over Na2SO4
6. filtrationfiltered
7. customThe solvent was removed under reduced pressure
8. customthe residual oil was chromatographed (CH2Cl2/EtOAc)

ORDレコード

ord-88badfb1c2d54cc0a743e9f40cbe5eb1

出典データセット

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09303015B2