3-amino-N,N-dimethylbenzylamine → US9701664, Example 124

온도

100 °C

A mixture of 6-chloro-N-(5-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-methylphenyl)nicotinamide (50 mg, 0.12 mmol),3-((dimethylamino)methyl)aniline (26.6 mg, 0.18 mmol),(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.10 mg, 7.08 µmol),TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (3.24 mg, 3.54 µmol),sodium 2-methylpropan-2-olate (17.01 mg, 0.18 mmol) in toluene (2 mL)/IPA (0.500 mL)was degassed with nitrogen and heated at reflux for 18 hours.The reaction mixture was filtered and filtered solid washed with ethyl acetate. The organic filtrate was washed with water (50ml), and organic layer dried over Na2SO4, filtered and evaporated. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N-(5-(2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamido)-2-methylphenyl)-6-(3-((dimethylamino)methyl)phenylamino)nicotinamide (24.60 mg, 38.8 %) as a cream solid.

ORD 기록

ord-6b87f2a7230043c19d1f4cb86bf0930a

출처 데이터셋

750 AstraZeneca ELN dataset

원본 링크

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