1-Hydroxybenzotriazole → HCID 59140113, compound

To a solution of 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid (2.0 g, 5.7 mmol) and O-(2-vinyloxyethyl)-hydroxylamine (0.71 g, 6.8 mmol) in DMF (44 mL) was added EDCI hydrochloride (1.42 g, 7.41 mmol), HOBt (1.0 g, 7.41 mmol) and DIPEA (0.97 mL, 5.69 mmol). The reaction mixture was stirred at room temperature for 3 hours before being concentrated in vacuo. The resultant residue was dissolved in 1:1 diethylether:ethyl acetate (30 mL) and aqueous saturated sodium hydrogen carbonate solution (30 mL) was added. The resultant mixture was sonicated until a precipitate formed. The precipitate was collected by filtration and washed with 1:1 diethylether:ethyl acetate to yield the title compound as a tan solid (1.33 g, 53%). LCMS (Method B): RT=2.78 min, M+H+=435/437.

1. concentrationbefore being concentrated in vacuo
2. dissolutionThe resultant residue was dissolved in 1:1 diethylether
3. additionethyl acetate (30 mL) and aqueous saturated sodium hydrogen carbonate solution (30 mL) was added
4. customThe resultant mixture was sonicated until a precipitate
5. customformed
6. filtrationThe precipitate was collected by filtration
7. washwashed with 1:1 diethylether

ORD record

ord-ace8cc062edf4c0cb25746de5124ab8a

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923456B2