Hydrochloric Acid → 2-(4-(2-Hydroxyethyl)-piperazin-1-yl)-thiazole-5-carboxylic acid hydroxyamide

To a solution of compound 15c (125 mg, 0.461 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (320 mg, 4.61 mmol) and a freshly prepared solution of sodium methoxide in methanol (159 mg, 6.91 mmol of sodium dissolved in 1.5 mL of methanol) under a N2 atmosphere. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was acidified to pH˜6 with 1M HCl and the formed precipitates were filtered off. The filtrate was diluted with ethyl acetate (5 mL) and water (2 mL) and the organic layer was separated. The aqueous layer was washed with ethyl acetate (5 mL) and the combined organic layers were dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 16c.

1. customthe formed precipitates
2. filtrationwere filtered off
3. additionThe filtrate was diluted with ethyl acetate (5 mL) and water (2 mL)
4. customthe organic layer was separated
5. washThe aqueous layer was washed with ethyl acetate (5 mL)
6. customthe combined organic layers were dried on sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by preparative HPLC

ORD record

ord-77c787c90a814e39b599ad4414c23e33

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345043B2