1,2-Dichloroethane → 1,1-Dimethylethyl 2-[(5-methyl-1,3-thiazol-4-yl)carbonyl]hydrazinecarboxylate

A solution of 5-methyl-1,3-thiazole-4-carboxylic acid (500 mg, 3.49 mmol) in dry dichloromethane (DCM) (17.500 ml) was stirred at room temperature under an atmosphere of argon. EDC (736 mg, 3.84 mmol) and HOBt (267 mg, 1.746 mmol) were added to the stirred solution and the resulting solution was stirred at room temperature for ½ hour. After this time, 1,1-dimethylethyl hydrazinecarboxylate (554 mg, 4.19 mmol) was added and the solution was stirred for a further 16 hours (overnight) at room temperature. The solution was diluted with DCM (approx. 50 ml) and washed with water (2× approx. 25 ml). The organics were dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow coloured oily solid. The residue was chromatographed [SiO2, MeOH in DCM 0-5%] to give a pale yellow coloured solid of desired material in 544 mg.

1. stirringthe solution was stirred for a further 16 hours (overnight) at room temperature
2. washwashed with water (2× approx. 25 ml)
3. dry with materialThe organics were dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customto give a yellow coloured oily solid
7. customThe residue was chromatographed [SiO2, MeOH in DCM 0-5%]
8. customto give a pale yellow coloured solid of desired material in 544 mg

ORD record

ord-be0cdf484189403cbfa25ecd2e6d2382

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2