ethyl 2-isocyanatobenzoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared from 5-[4-(3-aminopropyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one and 2-isocyanatobenzoic acid ethyl ester analogous to Example 214. Cyclization to the quinazoline occurs during the TMS-ethyl deprotection step. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (dq, J=7.71, 7.54 Hz, 2 H) 2.51-2.56 (m, 2 H) 3.92 (d, J=7.33 Hz, 2 H) 4.00 (s, 2 H) 6.63 (dd, J=8.08, 2.02 Hz, 1 H) 6.70 (d, J=2.02 Hz, 1 H) 7.17 (d, J=7.83 Hz, 2 H) 7.26 (d, J=8.08 Hz, 1 H) 7.61 (dd, J=15.41, 1.26 Hz, 1 H) 7.91 (dd, J=8.34, 1.52 Hz, 1 H) 8.93 (br. s., 1 H) 11.36 (br. s., 1 H)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared from 5-[4-(3-aminopropyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one and 2-isocyanatobenzoic acid ethyl ester analogous to Example 214. Cyclization to the quinazoline occurs during the TMS-ethyl deprotection step. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (dq, J=7.71, 7.54 Hz, 2 H) 2.51-2.56 (m, 2 H) 3.92 (d, J=7.33 Hz, 2 H) 4.00 (s, 2 H) 6.63 (dd, J=8.08, 2.02 Hz, 1 H) 6.70 (d, J=2.02 Hz, 1 H) 7.17 (d, J=7.83 Hz, 2 H) 7.26 (d, J=8.08 Hz, 1 H) 7.61 (dd, J=15.41, 1.26 Hz, 1 H) 7.91 (dd, J=8.34, 1.52 Hz, 1 H) 8.93 (br. s., 1 H) 11.36 (br. s., 1 H)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Carboethoxy-phenylisocyanate (0.20 g, 1.0 mmol) was prepared by the reaction of 2-carboethoxyaniline and triphosgene in toluene at reflux, followed by removing the solvent in vacuo. The isocyanate and the compound resulting from Example 1B (0.24 g, 1.0 mmol) were combined in 40 mL of toluene and heated at reflux for 3 hours. The product was then partitioned between 5% NaHCO3 and hot ethyl acetate, and the organic phase was dried (K2CO3) and evaporated. The resulting product was converted to its hydrochloride salt and recrystallized from ethanol-ether to yield 0.12 g of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.92 (d, 1H), 7.65 (t, 1H), 7.12-7.27 (m, 2H), 7.08 (t, 1H), 6.72 (dd, 2H), 4.02 (t, 2H), 3.73 (s, 3H), 3.12-3.3 (m, 3H), 2.52-2.65 (m, 3H), 2.38-2.48 (m, 2H), 2.1-2.3 (m, 2H), 1.57-1.68 (m, 1H), 1.37-1.5 (m, 1H). Anal calcd for C23H25N3O3 ·HCl·H2O: C, 61.95; H, 6.33; N, 9.42. Found: C, 61.94; H, 6.10; N, 9.18. at reflux by removing the solvent in vacuo heated at reflux for 3 hours The product was then partitioned between 5% NaHCO3 and hot ethyl acetate the organic phase was dried (K2CO3) evaporated recrystallized from ethanol-ether

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The compound (0.15 g) obtained in Example 404 and ethyl 2-isocyanatobenzoate (0.076 mg) were reacted and treated in the same manner as in the method described in Example 6 excluding Et3N to obtain the title compound as pale yellow oil (0.139 g, 64%). treated in the same manner as in the method

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is prepared from 5-[4-(3-aminopropyl)-2-benzyloxyphenyl]-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one and 2-isocyanatobenzoic acid ethyl ester analogous to Example 214. Cyclization to the quinazoline occurs during the TMS-ethyl deprotection step. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (dq, J=7.71, 7.54 Hz, 2 H) 2.51-2.56 (m, 2 H) 3.92 (d, J=7.33 Hz, 2 H) 4.00 (s, 2 H) 6.63 (dd, J=8.08, 2.02 Hz, 1 H) 6.70 (d, J=2.02 Hz, 1 H) 7.17 (d, J=7.83 Hz, 2 H) 7.26 (d, J=8.08 Hz, 1 H) 7.61 (dd, J=15.41, 1.26 Hz, 1 H) 7.91 (dd, J=8.34, 1.52 Hz, 1 H) 8.93 (br. s., 1 H) 11.36 (br. s., 1 H)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Carboethoxy-phenylisocyanate (0.20 g, 1.0 mmol) was prepared by the reaction of 2-carboethoxyaniline and triphosgene in toluene at reflux, followed by removing the solvent in vacuo. The isocyanate and the compound resulting from Example 1B (0.24 g, 1.0 mmol) were combined in 40 mL of toluene and heated at reflux for 3 hours. The product was then partitioned between 5% NaHCO3 and hot ethyl acetate, and the organic phase was dried (K2CO3) and evaporated. The resulting product was converted to its hydrochloride salt and recrystallized from ethanol-ether to yield 0.12 g of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.92 (d, 1H), 7.65 (t, 1H), 7.12-7.27 (m, 2H), 7.08 (t, 1H), 6.72 (dd, 2H), 4.02 (t, 2H), 3.73 (s, 3H), 3.12-3.3 (m, 3H), 2.52-2.65 (m, 3H), 2.38-2.48 (m, 2H), 2.1-2.3 (m, 2H), 1.57-1.68 (m, 1H), 1.37-1.5 (m, 1H). Anal calcd for C23H25N3O3 ·HCl·H2O: C, 61.95; H, 6.33; N, 9.42. Found: C, 61.94; H, 6.10; N, 9.18. at reflux by removing the solvent in vacuo heated at reflux for 3 hours The product was then partitioned between 5% NaHCO3 and hot ethyl acetate the organic phase was dried (K2CO3) evaporated recrystallized from ethanol-ether