Hydrazine hydrate (1:1) → HCID 178433740, compound

Temperature

100 °C

A suspension of 4-(2,4-difluorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxamide (180 mg, 0.442 mmol, 0.5 equiv DMF adduct) obtained above in 1,1-Dimethoxy-N,N-dimethylmethanamine (3 mL) was stirred for 1 h at 100° C. and then the mixture was concentrated under reduced pressure. The residue was dissolved in AcOH (3 mL) and then was added hydrazine monohydrate (108 μL, 2.21 mmol). The resulting mixture was stirred for 1 h at 100° C. and then concentrated under reduced pressure. To the residue, were added a 1:1 mixture of EtOAc and THF (20 mL) and saturated aqueous solution of sodium bicarbonate (15 mL) and then the organic layer was separated, which was washed with brine (5 mL) and dried over anhydrous sodium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was crystallized from THF (3 mL) and hexane (6 mL) to obtain title compound (147 mg, 84%) as a yellow solid.

1. concentrationthe mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in AcOH (3 mL)
3. stirringThe resulting mixture was stirred for 1 h at 100° C.
4. concentrationconcentrated under reduced pressure
5. additionTo the residue, were added
6. additiona 1:1 mixture of EtOAc and THF (20 mL) and saturated aqueous solution of sodium bicarbonate (15 mL)
7. customthe organic layer was separated
8. washwhich was washed with brine (5 mL)
9. dry with materialdried over anhydrous sodium sulfate
10. customInsoluble materials were removed by filtration
11. concentrationthe filtrate was concentrated under reduced pressure
12. customThe residue was crystallized from THF (3 mL) and hexane (6 mL)

ORD record

ord-e8534ae8cb6f41dc81c09793ca9a7370

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139589B2