1-Hydroxybenzotriazole → N-Cyclopropyl-4'-(5-{[(cyclopropylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1'-biphenyl-3-carboxamide

https://huagongshe.com/ko/reaction/31488

참여 물질

역할	이름	HCID	투입량
반응물	1-Hydroxybenzotriazole	HCID 75771	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	Cyclopropaneacetic acid	HCID 138440	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	4'-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1'-biphenyl-3-carboxamide	HCID 9997891	—
용매	Dimethylformamide	HCID 6228	—
생성물	N-Cyclopropyl-4'-(5-{[(cyclopropylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1'-biphenyl-3-carboxamide	HCID 11743420	—

반응 단계

Cyclopropylacetic acid (8.6 mg) and HATU (33 mg) in DMF (1 ml) were stirred for 10 minutes at room temperature. To this solution was added HOBt (11.6 mg), DIPEA (.0.45 ml) and 4′-[5-(aminomethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-6-methyl-1,1′-biphenyl-3-carboxamide (Example 53) (30 mg) in DMF (2 ml) and the reaction stirred at room temperature for 18 hours. The solvent was evaporated under vacuum and the residue dissolved in DCM and washed with water (2×4 ml). The organic phase was reduced to dryness and the residue purified by bond-elut (SCX, 5 g) eluting with methanol and methanolic ammonia. The methanolic ammonia fraction was further purified by preparative HPLC to give, after evaporation of the solvents, N-cyclopropyl-4′-(5-{[(cyclopropylacetyl)amino]methyl}-1,3,4-oxadiazol-2-yl)-6-methyl-1,1′-biphenyl-3-carboxamide.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US07425555B2
출처 데이터셋	uspto-grants-2008_09
ORD ID	ord-cee9229187bc4191bddab0d779521d5f
출처 메모	uspto-grants-2008_09