(R)-1-Methyl-10-((R)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one → (S)-1-Methyl-10-((R)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one

Participants

Reaction Steps

Using a similar procedure as described in Example #162, Step F-G, (S)-1-Methyl-10-((R)-3-methyl-pyrrolidin-3-yl)-3,5-dihydro-10H-6-oxa-3,4,10,11b-tetraaza-cyclopenta[b]phenanthren-2-one (SFC (Table 1, Method 54) Rt=4.016 min, 0.019 g, 6%) was prepared from (R)-3-((S)-7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-3-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (Example #164, Step B, isomer D, SFC (Table 1, Method 54), Rt=1.752 min, 0.45 g, 0.9 mmol). 1H NMR (400 MHz, methanol-d4) δ 7.37 (s, 1H), 7.23 (s, 1H), 7.19 (s, 1H), 6.46 (s, 1H), 5.05 (q, J=6.4 Hz, 1H), 4.58 (m, 2H), 4.04 (d, J=12.0 Hz, 1H), 3.79 (d, J=12.0 Hz, 1H), 3.59-3.43 (m, 2H), 2.98 (m, 1H), 2.68 (m, 1H), 1.76 (s, 3H), 1.49 (d, J=6.8 Hz, 3H). LC/MS (Table 1, Method 4) Rt=1.290 min; MS (ESI): m/z 340 [M+H]+.

Provenance & Evidence