1,2-Benzisoxazole-5-carboxylicacid,3-amino-,methylester(9CI) synthesis

Yield:737802-51-6 84%

Reaction Conditions:

with hydrogenchloride in methanol at 20; for 48 h;

Steps:

152.C Example 152; N-{3-[1-(3-Amino-benzo[d]isoxazol-5-yl)-1-ethyl-propyl]-1H-indol-7-yl}-methanesulfonamide; C. Preparation of : 3-Amino-benzo[d]isoxazole-5-carboxylic acid methyl ester

3-CYANO-4-ISOPROPYLIDENEAMINOOXY-BENZOIC acid methyl ester (1.20 g, 5.17 mmol) is dissolved in a saturated solution OF HCL in MEOH (35 mL). After stirring at room temperature for 2 d, the reaction is concentrated under reduced pressure, then added saturated aqueous NaHCO3 (100 mL) and EtOAc (100 mL) are added. The layers are separated, and the organic layer dried (MGS04), filtered and concentrated under reduced pressure. The crude residue is triturated with CH2Cl2 (30 mL), and the filtrate concentrated under reduced pressure and triturated with 7: 3 CH2C12 (6 mL). The solids are combined to afford the sub-title compound (832 mg, 84%). H NMR (300 MHz, DMSO-D6) # 3.88 (s, 3H), 6.64 (br s, 2H), 7.56 (dd, J= 0.6, 8.8 Hz, 1H), 8.10 (DD, J= 1.7, 8.8 Hz, 1H), 8.62 (dd, J= 0.6, 1.7 Hz, 1H). ESI MS m/z 193 [C9H8N2O3 + H]

References:

WO2004/67529,2004,A1 Location in patent:Page 195