Cesium carbonate → tert-butyl ((1S,2R)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclohexyl)carbamate

関与物質

役割	名称	HCID	仕込み量
反応物	Cesium carbonate	HCID 10796	—
反応物	tert-butyl N-[(1S,2S)-2-aminocyclohexyl]carbamate	HCID 1514391	—
反応物	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
反応物	2-Chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline	HCID 89921772	—
触媒	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
溶媒	Dimethylacetamide	HCID 31374	—
生成物	tert-butyl ((1S,2R)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclohexyl)carbamate	HCID 118043439	45.3%

反応条件

温度	125 °C

反応手順

A mixture of 2-chloro-6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazoline (0.1 g, 0.27 mmol), tert-butyl ((1S,2S)-2-aminocyclohexyl)carbamate (75 mg, 0.35 mmol), Cs2CO3 (176 mg, 0.54 mmol), X-Phos (13 mg, 0.027 mmol) and Pd2dba3 (12.5 mg, 0.013 mmol) in DMA (1.8 mL) was degassed with N2 for 5 mins and heated in a microwave reactor at 125° C. for 30 mins. The mixture was cooled to room temperature, filtered through celite and washed with water followed by saturated brine solution. The residue was purified by silica gel column chromatography to afford tert-butyl ((1S,2R)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)cyclohexyl)carbamate (67 mg, 45%). MS (ES+) C27H32Cl2N4O4 requires: 546, found: 547 [M+H]+.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09434700B2
出典データセット	uspto-grants-2016_09
ORD ID	ord-bc6fea8b125d4e8ebe4d6b090353c70d
出典メモ	uspto-grants-2016_09