Triethylamine → HCID 54684181, compound

Participants

Reaction Steps

N-(2-{[(4-fluoro-3-methylbenzyl)amino]carbonyl}-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-d][1,4]diazepin-10-yl)-N,N′,N′-trimethylethanediamide (prepared as described in Example 11, Step 1-7) was dissolved in methanol and treated with triethylamine (2 eq.), [(1-ethoxycyclopropyl)oxy](trimethyl)silane and acetic acid pH=5.5. To the mixture was then added NaCNBH3 (4 eq.) and reaction was refluxed overnight. After cooling to room temperature, mixture was concentrated under reduced pressure and purified by prep RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant) affording desired compound as a white solid. 1H NMR (300 MHz, CD3CN) δ 12.67 (bs, 1H), 10.01 (bs, 1H), 7.49 (d, J=7.52 Hz, 1H), 7.45-7.40 (m, 1H), 7.21 (t, J=8.62 Hz, 1H), 5.51-5.41 (m, 2H), 4.76 (dd, J=14.6 Hz, J=6.86 Hz, 1H), 4.66 (dd, J=14.6 Hz, J=6.41 Hz, 1H), 4.27-4.00 (m, 4H), 3.51-3.36 (m, 2H), 3.27 (s, 3H), 3.19 (s, 3H), 3.17 (s, 3H), 2.46 (s, 3H), 1.37-1.31 (m, 2H), 1.19-1.10 (m, 2H); MS (ES) C25H31FN6O5 requires 514. Found: 515 (M+H+).

Provenance & Evidence