Sodium triacetoxyborohydride → {3-[1-(3-Benzyl-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-propyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

2-(1-Amino-propyl)-3-benzyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 26, 300 mg, 0.94 mmol) and (3-oxo-propyl)-carbamic acid tert-butyl ester (J. Med. Chem. 1985, 28, 317–323, 982 mg, 5.64 mmol) were dissolved in CH3OH (20 mL) and stirred for 1 h at 25° C. The mixture was then treated with NaBH(OAc)3 (1.19 g, 5.64 mmol) and stirred for 18 h. The reaction mixture was concentrated under vacuum and purified by preparative HPLC using a YMC S10 ODS 30×250 mm column affording the desired compound (300 mg, 73%) as a colorless film: 13C NMR (CD3OD, 100 MHz) δ 160.8, 160.49, 154.89, 144.86, 136.06, 129.09, 128.04, 126.52, 121.79, 117.72, 115.16, 111.60, 109.53, 79.20, 57.97, 44.32, 27.38, 26.55, 25.5, 7.58; LC/MS (ESI+) 440 (M++H).

Provenance & Evidence