4-Hydroxybenzaldehyde → HCID 178486497, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1,1-dimethylethyl 4-({[4-(5-amino-3-methyl-1H-pyrazol-4-yl)-2-(methyloxy)phenyl]oxy}methyl)piperidine-1-carboxylate (100 mg, 0.24 mmol) and 4-hydroxybenzaldehyde (44 mg, 0.36 mmol) was dissolved in TFA (1 mL) and heated to 75° C. for 15 h. After cooling to rt, the mixture was diluted with DMF and purified by preparative reverse phase HPLC. The fractions containing the desired product were concentrated and lyophilized to yield 4-{1-methyl-8-(methyloxy)-7-[(piperidin-4-ylmethyl)oxy]-3H-pyrazolo[3,4-c]isoquinolin-5-yl)phenol hydrogen trifluoroacetate (26.2 mg, 20% yield). 1H NMR (400 MHz, d6-DMSO): 8.64-8.54 (m, 1H), 8.28-8.18 (m, 1H), 7.64 (s, 1H), 7.57-7.54 (m, 2H), 7.49 (s, 1H), 6.95-6.91 (m, 2H), 4.05 (s, 3H), 3.82 (d, 2H), 3.31 (d, 2H), 2.92 (q, 2H), 2.81 (s, 3H), 2.16-2.04 (m, 1H), 1.94 (d, 2H), 1.53-1.42 (m, 2H); MS (EI) for C24H26N4O3: 419 (MH+).

Provenance & Evidence