(S)-quinuclidin-3-amine → (1aRS,7bSR)-5-{2-[((S)-1-azabicyclo[2.2.2]oct-3-yl)amino]benzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid

참여 물질

역할	이름	HCID	투입량
반응물	(S)-quinuclidin-3-amine	HCID 719216	—
반응물	(1aRS,7bSR)-5-(2-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid	HCID 86713249	—
용매	Dimethyl Sulfoxide	HCID 679	—
용매	Methanol	HCID 887	—
생성물	(1aRS,7bSR)-5-{2-[((S)-1-azabicyclo[2.2.2]oct-3-yl)amino]benzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid	HCID 71006841	13.8%

반응 조건

온도	140 °C

반응 단계

A solution of (1aRS,7bSR)-5-(2-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylic acid (Intermediate 67, 0.6 g) and (S)-1-azabicyclo[2.2.2]oct-3-ylamine (6.0 g) in DMSO (6 mL) was stirred and heated in a sealed vessel at 140° C. for 22 hours. After cooling, the mixture was diluted with methanol and concentrated under vacuum. The residue was purified by HPLC (C18) to give (1aRS,7bSR)-5-{2-[((S)-1-azabicyclo[2.2.2]oct-3-yl)amino]benzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid (0.107 g) as a white solid.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09290472B2
출처 데이터셋	uspto-grants-2016_03
ORD ID	ord-5c8ebed174c54c9cb2d0a2daa8e471fc
출처 메모	uspto-grants-2016_03