4'-amino-N-(tert-butyl)-3'-fluoro[1,1'-biphenyl]-2-sulfonamide -Drug Synthesis Database

【结构式】

【分子编号】47966

【品名】4'-amino-N-(tert-butyl)-3'-fluoro[1,1'-biphenyl]-2-sulfonamide

【CA登记号】

【分子式】C₁₆H₁₉FN₂O₂S

【分子量】322.4035432

【元素组成】C 59.61% H 5.94% F 5.89% N 8.69% O 9.93% S 9.95%

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：(XI)

Coupling of acid chloride (X) with the biphenyl amine (XI) gave the corresponding amide (XII). The tert-butyl and Boc protecting groups of (XII) were finally cleaved by treatment with trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Bostrom, L.L.; Pinto, D.J.P.; Galemmo, R.A. Jr.; Rossi, K.A. (DuPont Pharmaceuticals Co.); Nitrogen containing heteroaromatics with ortho-substd. P1's as factor Xa inhibitors. EP 1042299; WO 9932454 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(X)	47965	tert-butyl 2-[5-(chlorocarbonyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzylcarbamate	C₁₇H₁₇ClF₃N₃O₃	详情	详情
(XI)	47966	4'-amino-N-(tert-butyl)-3'-fluoro[1,1'-biphenyl]-2-sulfonamide	C₁₆H₁₉FN₂O₂S	详情	详情
(XII)	47967	tert-butyl 2-[5-[([2'-[(tert-butylamino)sulfonyl]-3-fluoro[1,1'-biphenyl]-4-yl]amino)carbonyl]-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzylcarbamate	C₃₃H₃₅F₄N₅O₅S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

The condensation of diketone (I) with hydrazine (II) in refluxing EtOH gave pyrazole (III). Carboxylic acid (IV) was then obtained by oxidative cleavage of the furan ring with KMnO4. After conversion of (IV) to the corresponding acid chloride (V), coupling with the biphenyl amine (VI) provided amide (VII). Ring closure of the fluoronitrile group with acetamidine hydrochloride (VIII) with concomitant deprotection of the N-tert-butyl group furnished the title aminoquinazoline derivative.

参考文献中间体

合成目标

【1】 Rossi, K.A.; Clark, C.G.; Li, R.; et al.; Discovery of aminoquinazoline and aminoindazole P1 side chains as benzamidine mimics for FXa inhibitors. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 50.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	47956	4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione; 1-(2-Furanyl)-4,4,4-trifluoro-1,3-butanedione	326-90-9	C₈H₅F₃O₃	详情	详情
(II)	49135	2-fluoro-5-hydrazinobenzonitrile		C₇H₆FN₃	详情	详情
(III)	49136	2-fluoro-5-[5-(2-furyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzonitrile		C₁₅H₇F₄N₃O	详情	详情
(IV)	49137	1-(3-cyano-4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid		C₁₂H₅F₄N₃O₂	详情	详情
(V)	49138	1-(3-cyano-4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride		C₁₂H₄ClF₄N₃O	详情	详情
(VI)	47966	4'-amino-N-(tert-butyl)-3'-fluoro[1,1'-biphenyl]-2-sulfonamide		C₁₆H₁₉FN₂O₂S	详情	详情
(VII)	49139	N-[2'-[(tert-butylamino)sulfonyl]-3-fluoro[1,1'-biphenyl]-4-yl]-1-(3-cyano-4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide		C₂₈H₂₂F₅N₅O₃S	详情	详情
(VIII)	15866	ethanimidamide		C₂H₆N₂	详情	详情

Extended Information