Methyl bromoacetate → (+/-)-(2-{1-[(3-tert-Butoxycarbonylaminopropyl)-(4-methylbenzoyl)-amino]-propyl}-4-oxo-4H-pyrrolo[2,1-f][1,2,4]triazin-3-yl)-acetic acid methyl ester

Participants

Reaction Steps

(±)-(3-{(4-Methylbenzoyl)-[1-(4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4] triazin-2-yl)-propyl]amino}propyl)carbamic acid tert-butyl ester (Example 3 A, 100 mg, 0.21 mmol) was converted to the title compound (35 mg, 31%) in a manner similar to the preparation of (±)-{3-[{1-[3-(4-fluorobenzyl)-4-oxo-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl]-propyl}-(4-methylbenzoyl)-amino]-propyl}-carbamic acid tert-butyl ester, except that methyl bromoacetate (42 mg, 0.27 mmol) was used instead of 4-fluorobenzyl bromide: 1H NMR (CDCl3) δ 7.43 (m, 1H), 7.26–7.21 (m, 4H), 7.07 (m, 1H), 6.58 (m, 1H), 5.84 (m, 1H), 5.10 (m, 1H), 4.78 (m, 1H), 3.91 (m, 1H), 3.78 (m, 3H), 3.71 (m, 1H), 3.31 (m, 2H), 2.74 (m, 2H), 2.40 (s, 3H), 2.21 (m, 1H), 2.05 (m, 1H), 1.52 (m, 1H), 1.39 (s, 9H), 1.04 (t, 3H, J=7.15 Hz); MS (ESI+) 540.21 (M++H).

Provenance & Evidence