Triethylamine → HCID 44435404, compound

Participants

Reaction Conditions

Reaction Steps

4-(3-aminophenylamino)-6-(2-morpholinoethylamino)-1,7-naphthyridine-3-carbonitrile (111 mg, 0.29 mmol, 1 eq) was suspended in methylene chloride (10 mL). Triethylamine (44 uL, 0.32 mmol, 1.1 eq) was added and the mixture was cooled to 0° C. Methylsulfonyl chloride (24 uL, 0.31 mmol, 1.1 eq) was added and the mixture was stirred at room temperature for 12 hr. Another 44 uL triethylamine (1.1 eq) and 48 uL methylsulfonyl chloride (2.2 eq) were added and reaction mixture was stirred for 12 hr. Work-up and preparative HPLC yielded 45.5 mg product (34% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 2.39-2.47 (m, 4 H) 2.56 (t, J=6.82 Hz, 2 H) 2.99-3.03 (m, 3 H) 3.27-3.42 (m, 2 H) 3.55-3.61 (m, 4 H) 6.63 (t, J=6.06 Hz, 1 H) 7.00-7.04 (m, 1 H) 7.04 (s, 1 H) 7.08 (d, J=8.59 Hz, 1 H) 7.12-7.16 (m, 1 H) 7.36 (t, J=8.34 Hz, 1 H) 8.26 (s, 1 H) 8.84 (s, 1 H) 9.69 (s, 2 H).

Provenance & Evidence