Dichloromethane → HCID 58027417, compound

Analogous to the general method described in J. Med. Chem., (2005), 48(6), 2134-2153. To a flask containing 2-methylthiazole-4-carboxylic acid (1.10 g, 7.68 mmol) was added DCM (30 mL) and the homogeneous solution was stirred at room temperature as carbonyldiimidazole (1.30 g, 8.02 mmol) was added. A white opaque suspension resulted. After the mixture was stirred at room temperature for 2.25 hours a colorless homogeneous solution resulted and then N,O-dimethylhydroxylamine hydrochloride (820 mg, 8.41 mmol) was added which caused an opaque solution to result once again. The mixture was stirred at room temperature for 18 hours, then diluted with water and 1 N NaOH (to pH ˜9) and extracted with DCM (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to give a colorless oil, which was passed through a plug of silica gel eluting with (20% THF-DCM) to provide the title compound as a colorless oil.

1. additionwas added
2. customA white opaque suspension resulted
3. customresulted
4. customto result once again
5. stirringThe mixture was stirred at room temperature for 18 hours
6. extractionextracted with DCM (4×50 mL)
7. washThe combined organics were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a colorless oil, which

ORD record

ord-df83df5105da486c96795b0d698396eb

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309222B2