4-Methylmorpholine → 5-Tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide

참여 물질

역할	이름	HCID	투입량
반응물	4-Methylmorpholine	HCID 7972	—
반응물	Potassium Hydroxide	HCID 14797	—
반응물	3,4-Dichlorophenethylamine	HCID 217958	—
반응물	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
반응물	Methyl 5-(tert-butyl)picolinate	HCID 10774153	—
용매	Tetrahydrofuran	HCID 8028	—
생성물	5-Tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide	HCID 67017702	58.1%

반응 단계

Potassium hydroxide (2 M aq. solution, 0.98 mL, 1.96 mmol) was added at RT to a solution of 5-tert-butyl-pyridine-2-carboxylic acid methyl ester (synthesized according to J. Org. Chem. 1998, 63, 7840-7850; 189 mg, 0.98 mmol) in THF (2.6 mL), then after stirring for 2 h, the reaction mixture was evaporated. The residue was taken up in DMF (12 mL), then after addition of 2-(3,4-dichloro-phenyl)-ethylamine (204 mg, 1.07 mmol), 4-methylmorpholine (297 mg, 2.93 mmol), and HBTU (556 mg, 1.47 mmol), the reaction mixture was stirred at RT for 16 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and concentrated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced 5-tert-butyl-pyridine-2-carboxylic acid [2-(3,4-dichloro-phenyl)-ethyl]-amide (200 mg, 58%). White solid, MS (ISP): 351.4 (M+H)+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07674815B2
출처 데이터셋	uspto-grants-2010_03
ORD ID	ord-457ea0d6351e45cea2190369d974942f
출처 메모	uspto-grants-2010_03