2-Chlorobenzothiazole → HCID 178420734, compound

Participants

Reaction Conditions

Reaction Steps

trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutanamine (78 mg, 0.42 mmol), 4-dimethylaminopyridine (3.56 mg, 0.029 mmol), N,N-diisopropylethylamine (159 μl, 0.916 mmol) and 2-chlorobenzothiazole (81 μl, 0.625 mmol) were added in a round bottomed flask, followed by dry DMSO (833 μl). The mixture was sealed and heated at 110° C. for 16 h. The reaction mixture was partitioned between water, saturated ammonium chloride and ethyl acetate. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using ISCO (0-60% EtOAc in hexane), gave N-(trans-3-(1H-pyrrolo[2,3-b]pyridin-1-yl)cyclobutyl)benzo[d]thiazol-2-amine (23 mg, 0.072 mmol, 17% yield) as off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 2.77 (ddd, J=14.04, 8.46, 3.72 Hz, 2 H) 2.96-3.14 (m, 2 H) 4.56 (dt, J=7.43, 3.72 Hz, 1 H) 5.59-5.76 (m, 1 H) 6.54 (d, J=3.52 Hz, 1 H) 7.04-7.17 (m, 2 H) 7.28-7.36 (m, 1 H) 7.45 (d, J=3.72 Hz, 1 H) 7.60 (t, J=8.51 Hz, 2 H) 7.92 (dd, J=7.82, 1.37 Hz, 1 H) 8.32 (dd, J=4.69, 1.37 Hz, 1 H).

Provenance & Evidence