(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protected → HCID 86689740, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-4-(6-ethyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid amide (218 mg, 0.785 mmol), and tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (336 mg, 1.57 mmol) were dissolved in N-methylpyrrolidinone (4 mL) and heated at 150° C. for 40 h. Additional tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (168 mg, 0.78 mmol) was added and the heating continued for 16 h more. The reaction mixture was cooled and concentrated in vacuo, then diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (sodium sulfate), filtered and concentrated in vacuo. Purification by chromatography (silica, 0 to 5% methanol in dichloromethane) gave {(1S,2R)-2-[6-carbamoyl-5-(6-ethyl-pyridin-2-ylamino)-pyridazin-3-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (167 mg, 46%) as a light brown amorphous residue. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 11.44 (s, 1H) 8.47 (s, 1H) 7.97-8.03 (m, 1H) 7.52 (t, J=7.6 Hz, 1H) 7.22-7.26 (m, 1H) 6.78 (d, J=7.2 Hz, 1H) 6.70 (d, J=7.9 Hz, 1H) 5.38-5.43 (m, 1H) 4.92-5.00 (m, 1H) 3.97-4.08 (m, 2H) 2.80 (q, J=7.6 Hz, 2H) 1.58-1.96 (m, 8H) 1.41 (s, 9H) 1.31-1.39 (m, 3H); LCMS (EI/CI) m/z: 456 [M+H].

Provenance & Evidence