P-Anisidine → HCID 56969137, compound

Participants

Reaction Conditions

Reaction Steps

(S)-4-(1-acetylpiperidin-3-ylamino)-6-chloronicotinamide (50 mg, 0.17 mmol), p-anisidine (31 mg, 0.26 mmol), Cs2CO3 (111 mg, 0.34 mmol), BINAP (16 mg, 0.026 mmol), and Pd(OAc)2 (4 mg, 0.017 mmol) and degassed dioxane (4 mL) were heated to 100° C. under Argon overnight. The following morning the mixture was determined to be complete by UPLC. The reaction was diluted with water, acetonitrile, and TFA, then purified by HPLC affording 4 mg of the desired product after lyophilization. MS found for C20H25N5O3 as (M+H)+ 384.3. UV: λ=202, 257 nm. 1H NMR: (CD3OD) (mixture of rotamers) δ 8.12 (s, 0.4H), 8.06 (s, 0.6H), 7.24 (dd, 2H), 7.06 (dd, 2H), 5.98 (s, 0.7H), 5.89 (s, 0.3H), 3.84 (s, 3H), 3.40-3.68 (m, 5H), 2.13 (s, 2H), 2.03 (m, 1H), 1.98 (s, 1H), 1.52-1.93 (m, 3H).

Provenance & Evidence