Ethanol → 4-Fluoro-6-{2-(methylamino)-6-[(3R)-3-methyl-4-morpholinyl]-4-pyrimidinyl}-1H-indazol-3-amine

Participants

Reaction Conditions

Reaction Steps

A 2-mL microwave vial was charged with 2,6-difluoro-4-{2-(methylamino)-6-[(3R)-3-methyl-4-morpholinyl]-4-pyrimidinyl}benzonitrile (75 mg, 0.217 mmol), hydrazine (0.027 mL, 0.869 mmol), Hunig's base (0.152 mL, 0.869 mmol) and ethanol (1 mL). The reaction mixture was heated at 150° C. for 15 minutes in a microwave reactor. The reaction mixture was allowed to cool, then was poured into EtOAc (50 mL) and water (25 mL). The aqueous layer was extracted with two further portion of EtOAc (2×50 mL), and the combined organics dried over Na2SO4. The dried solution was filtered and concentrated, and the resulting residue was purified by RP-HPLC (0-30% CH3CN in H2O, 0.1% TFA) to afford the title compound (53.2 mg) as a yellow solid. LC-MS (ES) m/z=358 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.19 (d, J=6.6 Hz, 3H), 2.83 (bs, 3H), 3.06-3.20 (m, 1H), 3.40-3.52 (m, 1H), 3.55-3.66 (m, 1H), 3.69-3.78 (m, 1H), 3.88-4.00 (m, 1H), 4.06-4.24 (m, 1H), 4.43-4.62 (m, 1H), 5.27 (bs, 2H), 6.45-6.71 (m, 2H), 7.26-7.49 (m, 1H), 7.76-7.96 (m, 1H), 11.71-12.13 (m, 1H).

Provenance & Evidence