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【结 构 式】

【分子编号】23450

【品名】4-(2-pyridinyl)benzoic acid

【CA登记号】

【 分 子 式 】C12H9NO2

【 分 子 量 】199.209

【元素组成】C 72.35% H 4.55% N 7.03% O 16.06%

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:(XIV)

2) Intermediate (IX) can also be obtained as follows: The cyclization of 4-cyanobenzoic acid methyl ester (XII) with acetylene at 15 Atm by means of cobaltocene in toluene at 180 C gives 4-(2-pyridyl)benzoic acid methyl ester (XIII), which is saponified with NaOH in methanol to the corresponding acid (XIV). The activation of (XIV) with isobutyl chloroformate yields the mixed anhydride (XV), which is condensed with N-(tert-butoxycarbonyl)-L-phenylalaninal (XVI) and KCN in dichloromethane, affording (XVII). The reaction of (XVII) with tert-butyl carbazate (V) by means of acetic acid in methanol gives hydrazone (XVIII), which is reduced to hydrazine (XIX) by means of sodium cyanoborohydride in THF. The isomerization of (XIX) by means of 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTDE) in hot diglyme yields hydrazide (XX), which is finally reduced to intermediate (IX) with diisobutylaluminum hydride in dichloromethane/THF.

1 Fassler, A.; Steiner, H.; Bold, G.; Capraro, H.-G. (Novartis AG); Process for the preparation of hydrazine derivs. useful as intermediates for the preparation of peptide analogues. WO 9746514 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 23634 acetylene 74-86-2 C2H2 详情 详情
(V) 10893 tert-butyl 1-hydrazinecarboxylate; tert-butyl carbazate 870-46-2 C5H12N2O2 详情 详情
(IX) 23445 tert-butyl 2-[(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl]-2-[4-(2-pyridinyl)benzyl]-1-hydrazinecarboxylate C32H42N4O5 详情 详情
(XII) 10169 methyl 4-cyanobenzoate;4-Cyanobenzoic acid methyl ester 1129-35-7 C9H7NO2 详情 详情
(XIII) 23449 methyl 4-(2-pyridinyl)benzoate C13H11NO2 详情 详情
(XIV) 23450 4-(2-pyridinyl)benzoic acid C12H9NO2 详情 详情
(XV) 23451 4-(2-Pyridyl)benzoic acid isobutoxycarbonyl anhydride C17H17NO4 详情 详情
(XVI) 14540 tert-butyl N-[(1S)-1-benzyl-2-oxoethyl]carbamate C14H19NO3 详情 详情
(XVII) 23453 (1R,2S)-2-[(tert-butoxycarbonyl)amino]-1-cyano-3-phenylpropyl 4-(2-pyridinyl)benzoate C27H27N3O4 详情 详情
(XVIII) 23454 tert-butyl 2-((E,2R,3S)-3-[(tert-butoxycarbonyl)amino]-4-phenyl-2-[[4-(2-pyridinyl)benzoyl]oxy]butylidene)-1-hydrazinecarboxylate C32H38N4O6 详情 详情
(XIX) 23455 tert-butyl 2-((2S,3S)-3-[(tert-butoxycarbonyl)amino]-4-phenyl-2-[[4-(2-pyridinyl)benzoyl]oxy]butyl)-1-hydrazinecarboxylate C32H40N4O6 详情 详情
(XX) 23457 tert-butyl 2-[(2S,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyl]-2-[4-(2-pyridinyl)benzoyl]-1-hydrazinecarboxylate C32H40N4O6 详情 详情
Extended Information