3-((R)-7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester → (R)-7-bromo-4-methyl-6-(3-methyl-azetidin-3-ylamino)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one

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Reaction Steps

A solution of 3-((R)-7-bromo-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (Example #148, Step G, 5 g, 10.4 mmol) in TFA (4 mL) and DCM (24 mL) was stirred at ambient temperature for 3 h. The solvent was removed in vacuo to give (R)-7-bromo-4-methyl-6-(3-methyl-azetidin-3-ylamino)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (4 g, 100%). 1H NMR (400 MHz, DMSO-d6) δ 10.77 (s, 1H), 7.19 (s, 1H), 5.83 (s, 1H), 5.55 (s, 1H), 4.91 (q, J=6.4 Hz, 1H), 4.51 (s, 2H), 4.05 (m, 4H), 1.55 (s, 3H), 1.25 (d, J=6.4 Hz, 3H). LC/MS (Table 1, Method 6) Rt=0.656 min.; MS m/z: 380 [M+H]+ and 382 [M+H+2]+.

Provenance & Evidence