Hydrochloric Acid → [3-(4-{[(phenylamino)carbonyl]amino}phenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid

Temperature

70 °C

A heterogeneous mixture of [3-(4-nitrophenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid (31.0 mmol), elemental tin dust (5.30 mmol), 6.0N aqueous hydrochloric acid (5.3 mL) and absolute ethanol (5.3 mL) was stirred at 70° C. for 1 h. The solution was filtered through Celite and concentrated in vacuo. The resulting aniline was dissolved in anhydrous pyridine (10 mL) and phenyl isocyanate (11.17 mmol) added dropwise. The reaction mixture was stirred at room temperature for 4 h. After concentration in vacuo, purification by Gilson reverse phase HPLC afforded the title compound as a white solid (93%). ESMS [M+H]+: 453.2

1. filtrationThe solution was filtered through Celite
2. concentrationconcentrated in vacuo
3. dissolutionThe resulting aniline was dissolved in anhydrous pyridine (10 mL)
4. stirringThe reaction mixture was stirred at room temperature for 4 h
5. concentrationAfter concentration
6. customin vacuo, purification by Gilson reverse phase HPLC

ORD record

ord-081ea8f9d80d4173820dad800e49db48

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605266B2