Diisopropylethylamine → HCID 131734885, compound

Participants

Reaction Steps

A mixture of N-methyl-N-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,4-oxazepan-6-amine ((0.114 g (0.283 mmol) 107.5, (3,5-dichloro-phenylamino)-acetic acid (0.0685 g (0.311 mmol) 107.b, and 1-hydroxybenzotriazole hydrate (9 mg (0.057 mmol) were dissolved in DMF (4 mL). The resulting solution was treated with N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (60 mg, 0.311 mmol) and DIEA (100 uL (0.566 mmol) and stirred at rt for 24 hr. The mixture was diluted with H2O and extracted with EtOAc (2×) and 1:1 EtOAc/THF (2×). The combined organics were washed with 10% citric acid and brine, dried over MgSO4, filtered, and concentrated, absorbing onto 3 g SiO2. Purification by flash column chromatography (ISCO 12 g SiO2, 40% EtOAc/hex then gradient to 100% EtOAc) afforded (2-(3,5-dichlorophenylamino)-1-(6-(methyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-1,4-oxazepan-4-yl)ethanone (0.179 g) 107.6 as a white solid. LCMS (ESI) m/z: 603.20 [M+H]+.

Provenance & Evidence