2-nitro-N-[3-(trifluoromethyl)phenyl]benzamide -Drug Synthesis Database

【结构式】

【分子编号】64309

【品名】2-nitro-N-[3-(trifluoromethyl)phenyl]benzamide

【CA登记号】

【分子式】C₁₄H₉F₃N₂O₃

【分子量】310.2323496

【元素组成】C 54.2% H 2.92% F 18.37% N 9.03% O 15.47%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(III)

The intermediate anthranilamide (IV) is prepared by two alternative methods. Acylation of 3-(trifluoromethyl)aniline (I) with 2-nitrobenzoyl chloride (II) yields benzamide (III). The nitro group of (III) is then reduced to the corresponding amine (IV) by catalytic hydrogenation over Pd/C (1). Alternatively, 3-(trifluoromethyl)aniline (I) is condensed with isatoic anhydride (V) to furnish directly anthranilamide (IV) (2). Finally, reductive alkylation of (IV) with pyridine-4-carbaldehyde (VI) employing NaBH3CN gives rise to the target pyridylmethyl amine.

参考文献中间体

合成目标

【1】 Manley, P.W.; Furet, P.; Bold, G.; Bruggen, J.; Mestan, J.; Meyer, T.; Schnell, C.R.; Wood, J.; Anthranilic acid amides: A novel class of antiangiogenic VEGF receptor kinase inhibitors. J Med Chem 2002, 45, 26, 5687.
【2】 Seidelmann, D.; Huth, A.; Manley, P.W.; Thierauch, K.-H.; Krüger, M.; Bold, G.; Haberey, M.; Furet, P.; Altmann, K.-H.; Mestan, J.; Menrad, A.; Ferrari, S.; Wood, J.M.; Hofmann, F. (Novartis AG; Schering AG); N-Aryl(thio)anthranilic acid amide derivs., their preparation and their use as VEGF receptor tyrosine kinase inhibitors. EP 1129075; JP 2002529453; US 6448277; WO 0027820 .

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)	26347	3-(trifluoromethyl)phenylamine; 3-(trifluoromethyl)aniline; 3-aminobenzotrifluoride	98-16-8	C₇H₆F₃N	详情	详情
(II)	21099	o-nitrobenzoyl chloride; 2-nitrobenzoyl chloride	610-14-0	C₇H₄ClNO₃	详情	详情
(III)	64309	2-nitro-N-[3-(trifluoromethyl)phenyl]benzamide		C₁₄H₉F₃N₂O₃	详情	详情
(IV)	64310	2-amino-N-[3-(trifluoromethyl)phenyl]benzamide		C₁₄H₁₁F₃N₂O	详情	详情
(V)	29797	2H-3,1-benzoxazine-2,4(1H)-dione；Isatoic anhydride;4H-3,1-Benzoxazine-2,4(1H)-dione；1,2-Dihydro-4H-3,1-benzoxazine-2,4-dione;1H-benzo[d][1,3]oxazine-2,4-dione	118-48-9	C₈H₅NO₃	详情	详情
(VI)	17203	4-Pyridinecarboxaldehyde; isonicotinaldehyde	872-85-5	C₆H₅NO	详情	详情

Extended Information