3-Fluorobenzyl bromide → (+/-)-{3-[{1-[3-(3-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

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, 42 mg, 0.09 mmol) was converted to the title compound (7 mg, 13%) 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 3-fluorobenzyl bromide (22 mg, 0.12 mmol) was used instead of 4-fluorobenzyl bromide: 1H NMR (CDCl3) δ 7.45–6.96 (m, 10H), 6.62 (m, 1H), 5.95 (m, 1H), 5.86 (m, 1H), 4.90 (m, 1H), 3.86 (m, 1H), 3.33 (m, 2H), 2.71 (m, 2H), 2.39 (s, 3H), 2.05 (m, 1H), 1.85 (m, 1H), 1.60 (m, 1H), 1.40 (s, 9H), 1.05 (m, 1H), 0.72 (m, 3H).

Provenance & Evidence