(S)-(+)-1-Aminopropan-2-ol → 4-[(3-chloro-4-fluorophenyl)amino]-6-{[(2S)-2-hydroxypropyl]amino}-1,7-naphthyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Following the procedure described above in Example 51, 4-(3-Chloro-4-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile (0.10 g, 0.32 mmol) was reacted with (S)-1-amino-2-propanol (0.47 g, 6.32 mmol) in 2 mL of THF. The reaction mixture was heated up in a sealed vial in a microwave reactor at 140° C. for 40 min. The crude product was purified by preparative HPLC and lyophilized to give a yellow solid (20.8 mg, 17.7% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 0.93 (d, J=6.32 Hz, 3 H) 2.96-3.03 (m, 2 H) 3.68 (s, 1 H) 4.58 (s, 1 H) 6.46 (m, 1 H) 6.80 (s, 1 H) 7.06-7.17 (m, 1 H) 7.21-7.33 (m, 1 H) 7.33-7.47 (m, 1 H) 8.05 (s, 1 H) 8.62 (s, 1 H) 9.44 (s, 1 H); HRMS (ESI+) calcd for C18H15ClFN5O 372.10219, found (MH+) 372.1019.

Provenance & Evidence