Isopropylamine → HCID 60631570, compound

Participants

Reaction Steps

Using analogous procedures to those described in the portion of Note [9] immediately above that is concerned with the preparation of starting materials, 5-bromo-2-nitropyridine was reacted with isopropylamine to give 5-isopropylamino-2-nitropyridine in 93% yield; 1H NMR: (CDCl3) 1.3 (d, 6H), 3.74 (m, 1H), 4.46 (br s, 1H), 6.9 (m, 1H), 7.84 (m, 1H), 8.15 (d, 1H); Mass Spectrum: M+H+ 182; which in turn was converted into 5-(N-tert-butoxycarbonyl-N-isopropylamino)-2-nitropyridine in 84% yield; 1H NMR: (CDCl3) 1.19 (d, 6H), 1.4 (s, 9H), 4.55 (m, 1H), 7.76 (m, 1H), 8.26 (m, 1H), 8.38 (m, 1H); Mass Spectrum: M+H+ 282; which in turn was converted into 2-amino-5-(N-tert-butoxycarbonyl-N-isopropylamino)pyridine in 84% yield; 1H NMR: (CDCl3) 1.05 (d, 6H), 1.36 (br s, 9H), 4.46 (br s, 2H), 6.48 (d, 1H), 7.14 (m, 1H), 7.78 (m, 1H); Mass Spectrum: M+H+ 252; and which in turn was converted into N-[5-(N-tert-butoxycarbonyl-N-isopropylamino)pyridin-2-yl]-2-[4-(6,7-dimethoxyquinazolin-4-yloxy) phenyl]acetamide; Mass Spectrum: M+H+ 560.

Provenance & Evidence