p-Toluenesulfonic acid monohydrate → HCID 69262583, compound

Participants

Reaction Steps

A mixture of 7-[(2-amino-pyridine-3-carbonyl)-amino]-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (1.0 g, 2.5 mmol), 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (730 mg, 5.0 mmol), and p-toluenesulfonic acid monohydrate (48 mg, 0.25 mmol) in 50 mL of anhydrous toluene was stirred at reflux for 1 h. After being cooled to RT, the mixture was diluted with 2 mL of MeOH and NaBH4 (475 mg, 12.5 mmol) was added, and the mixture was stirred at RT for 30 min. The reaction was quenched with MeOH, and the volatiles were removed under reduced pressure. The residue was taken up in water, AcOH was added to bring pH to 4, and the mixture was extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, and condensed. The residue was purified by flash column chromatography to give 4,4-dimethyl-7-({2-[(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amino]-pyridine-3-carbonyl}-amino)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester. MS (ES+): 527.2 (M+H)+. Calc'd for C30H34N6O3 526.27.

Provenance & Evidence