L-Alaninol → 3-((3S,4S)-3-Fluoro-tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-(3-chloro-4-cyano-phenyl)-(1-methyl-1H-pyrazol-4-yl)-methyl]-amide

Participants

Reaction Steps

3-((3S,4S)-3-Fluoro-tetrahydro-pyran-4-ylamino)-isoquinoline-6-carboxylic acid [(S)-(3-chloro-4-cyano-phenyl)-(1-methyl-1H-pyrazol-4-yl)-methyl]-amide (II-59) was prepared analogously except in step 2, (S)-2-aminopropan-1-ol was replaced with (3S,4S)-3-fluorotetrahydro-2H-pyran-4-amine (71c) and in step 5, 50c was replaced with (S)-4-(amino(1-methyl-1H-pyrazol-4-yl)methyl)-2-chlorobenzonitrile hydrochloride (44). 1H NMR (500 MHz, DMSO-d6) δ 9.39 (d, J=8.0 Hz, 1H), 8.94 (s, 1H), 8.11 (s, 1H), 7.99 (d, J=8.5 Hz, 1H), 7.87 (d, J=9.0 Hz, 1H), 7.81 (s, 1H), 7.63-7.55 (m, 3H), 7.41 (s, 1H), 6.89 (s, 1H), 6.69 (d, J=8.0 Hz, 1H), 6.38 (d, J=8.0 Hz, 1H), 4.78 (d, J=49.5 Hz, 1H), 4.25-4.19 (m, 1H), 4.01 (t, J=13.0 Hz, 1H), 3.93-3.90 (m, 1H), 3.79 (s, 3H), 3.67-3.49 (m, 3H), 1.91-1.83 (m, 1H), 1.73-1.70 (m, 1H); LCMS (ESI) m/z: 519.2 [M+H]+.

Provenance & Evidence