Reaction #73039

Reaction equation

4-chloro-3-nitroquinoline

triethyl orthopropionate

1-(aminomethyl)cyclopropanol

1-(2-aminoethyl)cyclopropanol

trimethyl orthobutyrate

4-chloro-3-nitronaphthyridine

→

1-[(4-Amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]cyclopropanol

Conditions

Workup

1. 1
   OtherThe crude product was triturated with hot acetonitrile
2. 2
   Otherto provide a tan solid
3. 3
   OtherWhich was recrystallized from chloroform and hexanes
4. 4
   Otherdried at 140° C. under vacuum
5. 5
   Otherto provide product as an off-white solid, mp 199-200° C

Procedure

1-[(4-Amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)methyl]cyclopropanol was prepared according to the general methods of Parts D through G of Example 84 using 1-(aminomethyl)cyclopropanol in lieu of 1-(2-aminoethyl)cyclopropanol in Part D, 4-chloro-3-nitronaphthyridine in lieu of 4-chloro-3-nitroquinoline in Part D, and trimethyl orthobutyrate in lieu of triethyl orthopropionate in Part F. The crude product was triturated with hot acetonitrile to provide a tan solid. Which was recrystallized from chloroform and hexanes and dried at 140° C. under vacuum to provide product as an off-white solid, mp 199-200° C. MS (ESI) m/z 298 (M+H)+; Anal. calcd for C16H19N5O: C, 64.63; H, 6.44; N, 23.55. Found: C, 64.32; H, 6.62; N, 23.67.

Source