Oxalyl chloride → HCID 66677692, compound

4-Cyano-2-fluorobenzoic acid (ABCR, 1.65 g, 10 mmol) was dissolved in DCM (40 mL). DMF (8 μl) was added at RT followed by oxalyl chloride (0.98 mL, 11.6 mmol). Once the gas evolution has ceased, the reaction mixture was evaporated to dryness. The residue was then dissolved in DCM (10 mL) and beta-alanine ethyl ester hydrochloride (1.54 g, 10 mmol) was added followed by dropwise addition of N-ethyldiisopropylamine (3.40 mL, 20 mmol) over 10 minutes. The reaction mixture was then washed with water and a saturated aqueous solution of NaHCO3, dried with MgSO4 and evaporated in vaccuo affording the title compound (2.27 g, 86%) as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.67 (t, J=5.0 Hz, 1H), 7.97 (dd, J=10.0, 1.3 Hz, 1H), 7.79 (dd, J=7.9, 1.4 Hz, 1H), 7.71 (m, 1H), 4.08 (q, J=7.2 Hz, 2H), 3.49 (m, 2H), 2.57 (t, J=6.9 Hz, 2H), 1.19 (t, J=7.2 Hz, 3H). LC/MS (Method B): 263.2 (M−H)−. HPLC (Method A) Rt 2.68 min (Purity: 98.5%).

1. customthe reaction mixture was evaporated to dryness
2. dissolutionThe residue was then dissolved in DCM (10 mL)
3. washThe reaction mixture was then washed with water
4. dry with materiala saturated aqueous solution of NaHCO3, dried with MgSO4
5. customevaporated in vaccuo

ORD record

ord-77357c9e47fe4bf09640ef9d887b6fa8

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815919B2