Isocyanate → HCID 14626126, compound

Participants

Reaction Steps

To a solution of 4-amino-3-(diethylcarbamyloxy)-6,7-dimethoxy-1-methylisoquinoline (410.5 mg, 1.24 mmol) in methylene chloride (20 mL) was added n-butylisocyanate (2, 0.17 mL, 1.49 mmol, 1.2 eq.) and the solution was stirred at room temperature overnight. TLC analysis (40% ethyl acetate/chloroform) revealed the presence of a small amount of unreacted starting material. Therefore, additional isocyanate (0.17 mL, 1.49 mmol, 1.2 eq; total 0.34 mL, 2.98 mmol, 2.4 eq) was added and the mixture was stirred at room temperature overnight. Then the mixture was heated to reflux for an additional 48 hours. The crude mixture was separated on a low pressure silica gel column using ether/petroleum ether. Two products were isolated. The slower moving product is described in Example 6b. The faster moving product weighed 205 mg (31%) and had mp 138°-140° C. IR (KBr): 3360, 1700, 1650, 1610, 1500, 1420, 1142 cm-1 ; NMR (CDCl3): δ 0.85 (br t, J=7 Hz, 6H, N(CH2 -CH3)2 ], 1.10-1.70 [br m, 14H, N(CH2CH3)2 +H2C(CH2)2 -CH3 ], 2.88 (s, 3H, 1-CH3), 3.0-3.70 [m, 8H, CON(CH2CH3)2 +N[CH2 (CH2)2CH3 ]2, 3.95 (s, 3H, OCl4)3OCH3 4.02 (s, 3H, OCH3), 6.88 (s, 1H, 5- or 8-H), 7.27 (s, 1H, 5- or 8-H), 7.35 (m, 1H, CONH); MS (FAB): 532 (MH)+ ; UV (EtOH) nm: 241 (ε59060), 273 (ε4740), 286 (ε4700), 298 (ε4755), 322 (ε4390), 344 (ε4700).

Provenance & Evidence