Hydrochloric Acid → HCID 71736743, compound

Participants

Reaction Steps

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmol) and 3-amino-2-(S)-methyl-propionic acid, trifluoroacetic acid salt (48 mg, 0.47 mmol) in EtOH (2 mL) was added NaOMe solid (60 mg) (amount needed to adjust the pH of the mixture to 8-9). The resultant mixture was microwaved at 140° C. for 1 h. Reaction mixture was diluted with water (60 mL) and acidified by 1 N HCl to pH=3-4. It was extracted with EtOAc. Organic layer was dried over MgSO4, filtered and concentrated. Crude product was purified by silica gel chromatography, eluting with 5-100% EtOAc/CH2Cl2, to provide the title compound 16.8 mg (0.043 mmol) in 28% yield. 1H NMR (200 MHz) in DMSO-d6, δ ppm: 14.78 (s, 1H), 12.37 (s, 1H), 9.29 (br s, 1H), 8.41 (d, J=9.2 Hz, 1H), 7.73 (br d, J=10.6 Hz, 1H), 7.54 (m, 2H), 7.30 (m, 4H), 3.58 (m, 1H), 3.43 (m, 1H), 2.81 (m, 1H), 1.10 (d, J=7.0 Hz, 3H).

Provenance & Evidence