N-[4-(2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]ethyl)phenyl]-4-[4-[4-(trifluoromethyl)benzoyl]-2H-1,2,3-triazol-2-yl]benzenesulfonamide -Drug Synthesis Database

【结构式】

【分子编号】39312

【品名】N-[4-(2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]ethyl)phenyl]-4-[4-[4-(trifluoromethyl)benzoyl]-2H-1,2,3-triazol-2-yl]benzenesulfonamide

【CA登记号】

【分子式】C₃₁H₂₇F₃N₆O₄S

【分子量】636.6546296

【元素组成】C 58.48% H 4.27% F 8.95% N 13.2% O 10.05% S 5.04%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VIII)

2-Phenyl-1,2,3-triazole-4-carboxylic acid (I) was converted to acid chloride, which was further treated with N-methoxy-N-methylamine to provide the corresponding Weinreb amide (II). Subsequent chlorosulfonylation of (II) gave rise to sulfonyl chloride (III), which was coupled with the known amine (IV), yielding sulfonamide (V). The Boc protecting group of (V) was then cleaved by means of trifluroacetic acid to afford (VI). Addition of Grignard reagent (VII) to the N-methoxyamide (VI) furnished ketone (VIII).

参考文献中间体

合成目标

【1】 Parmee, E.R.; Ok, H.O.; Brockunier, L.L.; et al.; Human beta3-adrenergic receptor agonist containing 1,2,3-triazole-substituted benzenesulfonamides. Bioorg Med Chem Lett 2000, 10, 18, 2111.
【2】 Brockunier, L.L.; Parme, E.R.; Ok, H.O.; et al.; Human beta3 adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 252.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	39306	2-phenyl-2H-1,2,3-triazole-4-carboxylic acid	C₉H₇N₃O₂	详情	详情
(II)	39307	N-methoxy-N-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxamide	C₁₁H₁₂N₄O₂	详情	详情
(III)	39308	4-(4-[[methoxy(methyl)amino]carbonyl]-2H-1,2,3-triazol-2-yl)benzenesulfonyl chloride	C₁₁H₁₁ClN₄O₄S	详情	详情
(IV)	26553	tert-butyl 4-aminophenethyl[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]carbamate	C₂₀H₂₇N₃O₃	详情	详情
(V)	39309	tert-butyl (2R)-2-hydroxy-2-(3-pyridinyl)ethyl[4-([[4-(4-[[methoxy(methyl)amino]carbonyl]-2H-1,2,3-triazol-2-yl)phenyl]sulfonyl]amino)phenethyl]carbamate	C₃₁H₃₇N₇O₇S	详情	详情
(VI)	39310	2-(4-[[4-(2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]ethyl)anilino]sulfonyl]phenyl)-N-methoxy-N-methyl-2H-1,2,3-triazole-4-carboxamide	C₂₆H₂₉N₇O₅S	详情	详情
(VII)	39311	bromo[4-(trifluoromethyl)phenyl]magnesium	C₇H₄BrF₃Mg	详情	详情
(VIII)	39312	N-[4-(2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]ethyl)phenyl]-4-[4-[4-(trifluoromethyl)benzoyl]-2H-1,2,3-triazol-2-yl]benzenesulfonamide	C₃₁H₂₇F₃N₆O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

After reduction of (VIII) to alcohol (IX) with NaBH4, further alcohol reduction using triethylsilane and trifluoroacetic acid produced the title compound

参考文献中间体

合成目标

【1】 Parmee, E.R.; Ok, H.O.; Brockunier, L.L.; et al.; Human beta3-adrenergic receptor agonist containing 1,2,3-triazole-substituted benzenesulfonamides. Bioorg Med Chem Lett 2000, 10, 18, 2111.
【2】 Brockunier, L.L.; Parme, E.R.; Ok, H.O.; et al.; Human beta3 adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 252.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIII)	39312	N-[4-(2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]ethyl)phenyl]-4-[4-[4-(trifluoromethyl)benzoyl]-2H-1,2,3-triazol-2-yl]benzenesulfonamide		C₃₁H₂₇F₃N₆O₄S	详情	详情
(IX)	39313	N-[4-(2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]ethyl)phenyl]-4-(4-[hydroxy[4-(trifluoromethyl)phenyl]methyl]-2H-1,2,3-triazol-2-yl)benzenesulfonamide		C₃₁H₂₉F₃N₆O₄S	详情	详情

Extended Information