Hydrochloric Acid → HCID 89812843, compound

Participants

Reaction Steps

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (90 mg, 0.28 mmol) and 4-amino-2,2-dimethyl-butyric acid methyl ester, trifluoroacetic acid salt (290 mg, 1.12 mmol) in MeOH (0.5 mL) was added 0.5 M NaOMe/MeOH solution until the pH of the mixture reaches 8 (1.24 mL, 0.61 mmol was added). The resultant mixture was refluxed overnight. Reaction mixture was diluted with water (50 mL), acidified by 1 N HCl to pH=4 and then extracted with EtOAc. Organic layer was washed with brine, dried over MgSO4, filtered and concentrated. Residue was purified by silica gel chromatography, eluting with 5-50% EtOAc/hexnaes. Fractions containing the desired product were collected and concentrated. The resultant solid was triturated with MeOH (2 mL). Solid was collected and dried in vacuo to provide the title compound 23 mg (0.053 mmol) in 19% yield. LC-MS ESI−: 432.13 (M−1)−.

Provenance & Evidence