Hydrochloric Acid → HCID 69333506, compound

Participants

Reaction Steps

A mixture of ethyl 3-methoxy-4-[[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-N-[2-cyclopropylamino]ethylamino]ethoxy]benzoate (195 mg, 0.30 mmol)) in THF:MeOH(4:1, v/v) (5 mL) and 1N NaOH (0.756 mL) was stirred at 50 C. for 15 hr. The pH of the mixture was adjusted to 7.4 by the addition of 1N HCl, and extracted with CHCl3:MeOH(9:1, v/v). The extract was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was crystallized with Et2O to give 57 mg (38%) 3-methoxy-4-[[2-[3-methoxy-4-[N′-(2-methyl phenyl)ureido]phenylacetyl]-[2-cyclopropylamino]ethylamino]ethoxy]benzoic acid 264 as a white crystalline material. mp 135-140° C.; IR (KBr), 3324, 2937, 1535, 1032, 754 cm−1; 1H-NMR (CD3OD, 400 MHz) δ0.50-0.73 (m, 4H), 2.29 (s, 3H), 2.53 (m, 1H), 2.98 (m, 1H), 3.21 (m, 1H), 3.58-3.88 (m, 11H), 3.91 (s, 1H), 4.09 (m, 1H), 4.25 (m, 1H), 6.76-6.92 (m, 3H), 7.01 (m, 1H), 7.18 (m, 2H), 7.60 (m, 3H), 8.00 (d, J=8.3 Hz, 1H); MS (FAB) m/z 591(M+H)+; Anal Calcd. for C32H38N4O7.3.0H2O, C, 59.62; H, 6.88; N, 8.69. Found, C, 59.25; H, 6.29; N, 8.29.

Provenance & Evidence