1,2-Dichloroethane → HCID 46215627, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of 4-chloro-2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]benzoic acid (260 mg, 0.619 mmol) in N,N-dimethylformamide (DMF) (20 mL) was added HOBT (114 mg, 0.742 mmol) and EDC (142 mg, 0.742 mmol) and the reaction mixture was stirred for 30 min. To this solution was added O-methoxylamine hydrochloride (62.0 mg, 0.742 mmol), and after 30 min the reaction was cooled to 0° C. and DIEA (0.323 mL, 1.856 mmol) was added. The reaction mixture was stirred at the room temperature over the weekend. Water (100 mL) followed by acetic acid (1 mL) were added and the reaction mixture was extracted with 2×50 ml of ethyl acetate. The organic layer was washed with 2×50 ml sat KHCO3, brine, dried over MgSO4 and evaporated. The resulting yellow oil was purified by flash column chromatography on silica gel using DCM:EtOAc (10% to 100%). 4-Chloro-2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide (85 mg, 0.180 mmol, 29.1% yield) was isolated as white foam. 1H NMR (400 MHz, DMSO-d6) ppm 1.27 (d, J=6.57 Hz, 6 H) 2.12 (s, 3 H) 3.70 (s, 3 H) 4.41 (quin, J=6.57 Hz, 1 H) 5.95 (s, 1 H) 6.66 (s, 1 H) 7.01-7.39 (m, 1 H) 7.55-7.88 (m, 2 H) 8.02 (s, 1 H) 8.60 (s, 1 H) 9.76 (br. s., 1 H) 12.01 (br. s., 1 H); HPLC Rt=2.50 min, MS (ESI): 449.0, 451.1 [M+H]+.

Provenance & Evidence