5-Nitro-2-Furoic Acid → N2 4-[4-(4-ethyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)piperi dino]phenyl-5-nitro-2-furamide

HRID 515410

反応式

HRID 515410 の反応式
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].OC1C2N=[N:19][NH:18]C=2C=CC=1.C([N:24]=C=NCCCN(C)C)C.N[C:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]3[O:50][C:49](=[O:51])[N:48]([CH2:52][CH3:53])[N:47]=3)[CH2:42][CH2:41]2)=[CH:36][CH:35]=1>CN(C=O)C>[N:18]#[N:19].[CH2:52]([N:48]1[C:49](=[O:51])[O:50][C:46]([CH:43]2[CH2:42][CH2:41][N:40]([C:37]3[CH:38]=[CH:39][C:34]([C:6]4[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[O:8][C:7]=4[C:9]([NH2:24])=[O:11])=[CH:35][CH:36]=3)[CH2:45][CH2:44]2)=[N:47]1)[CH3:53]

参加物

6

反応物 4

HCID 125775-Nitro-2-Furoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 89650876HCID 89650876、化合物HCID 178418300HCID 178418300、化合物

生成物 1

HCID 131733297N2 4-[4-(4-ethyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)piperi dino]phenyl-5-nitro-2-furamide収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
27 °C

実験手順

5-[1-(4-Nitrophenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (5a, 1.16 g, 4 mmol) on reacting with C2H5Br (0.53 g, 4.8 mmol) in DMF in the presence of base K2CO3 (1.38 g, 10 mmol) at room temperature (27° C.) for 10 h, after completion of the reaction, reaction mixture is poured into ice water and extracted into chloroform finally purification by column chromatography to afford pure compound 3-ethyl-5-[1-(4-nitro phenyl)-4-piperidyl]-2,3-dihydro-1,3,4-oxadiazol-2-one (6b, 1.17 g, 92%). Nitro compound (6b, 1.27 g, 4 mmol) on reduction with SnCl2.2H2O (2.71 g, 12 mmol) in methanol and refluxed at 65° C. for 4 h, after completion of reaction methanol is evaporated under vacuum and to this saturated sodium bicarbonate solution is added to quench the excess stannous chloride and filtered through celite bed and purified in silica column (60-120) to afforded pure compound 5-[1-(4-aminophenyl)-4-piperidyl]-3-ethyl-2,3-dihydro-1,3,4-oxadiazol-2-one (7c, 1.02 g, 89%). To a stirred solution of 5-nitro2-furanoic acid in DMF add HOBT (Hydroxybenzotriazole) (0.14 g, 1 mmol), EDCI (1-Ethyl-3-(3-dimethylaminopropyl)carbodi imide)) (0.19 g, 1 mmol) and amine compound (7c, 0.29g, 1 mmol) and stirred for 2 h at room temperature (27° C.), after completion of the reaction, reaction mixture is poured into ice water and extracted into chloroform finally purification by column chromatography using ethyl acetate-hexane (7:3) as eluant to afford pure compound N2-4-[4-(4-ethyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)piperi dino]phenyl-5-nitro-2-furamide (8c, 367 mg, 86%).

後処理

  1. customafter completion of the reaction, reaction mixture
  2. extractionextracted into chloroform finally purification by column chromatography

出典と根拠

ORDレコード
ord-1b8d2959fdee42528274b853027bb989
出典データセット
uspto-grants-2015_08
特許番号
US09108960B2

関連ノート

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