p-(Trifluoromethoxy)benzaldehyde → 4-[5-(4-Trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]phenylamine

HRID 1475160ノート

反応式

HRID 1475160 の反応式
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)[O:16][N:15]=2)=[CH:10][CH:9]=1)(C)(C)C.C(OC(=O)NC1C=CC(C(=N)NO)=CC=1)(C)(C)C.FC(F)(F)OC1C=CC(C=O)=CC=1>C(O)(=O)C.C(Cl)(Cl)Cl>[F:29][C:26]([F:27])([F:28])[O:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[O:16][N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([NH2:7])=[CH:9][CH:10]=3)[N:18]=2)=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 66968928{4-[5-(4-Trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]-phenyl}-carbamic acid tert-butyl esterHCID 178452743HCID 178452743、化合物

生成物 1

HCID 578245054-[5-(4-Trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]phenylamine収率 15%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6212Chloroform溶媒

実験手順

{4-[5-(4-Trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]-phenyl}-carbamic acid tert-butyl ester. To a stirred solution of tert-butyl-4-(N-hydroxycarbamimidoyl)-phenylcarbamate (Ace Synthesis) (500 mg; 1.99 mmol) dissolved in 2.5 mL of acetic acid was added 4-trifluoromethoxybenzaldehyde (1.7 mL; 11.94 mmol), and the reaction mixture was stirred at room temperature for 4 d. The mixture was diluted with CHCl3 (20 mL) and filtered through a pad of Celite®. The pad was washed with CHCl3 (20 mL). Heptane (20 mL) was then added to the solution and the solution was concentrated under reduced pressure. This procedure was repeated twice. The residue was purified via radial chromatography using a 3:1 hexane/EtOAc solution as the eluent. Two fractions were isolated. The first fraction isolated (Rf=0.42) was shown to be the title compound (127 mg; 15%). 1H NMR (300 MHz, CDCl3) δ 8.26 (d, J=8.9 Hz, 2H), 8.09 (d, J=8.9 Hz, 2H), 7.52 (d, J=8.6 Hz, 2H), 7.39 (d, J=8.3 Hz, 2H), 6.70 (s, 1H), 1.54 (s, 9H); EI/MS 421 [M]+. The second fraction isolated (Rf=0.11) was shown to be the 4,5-dihydro-1,2,4-oxadiazole (96 mg; 11%). 1H NMR (300 MHz, CDCl3) δ 8.40 (d, J=8.9 Hz, 2 H), 8.00 (d, J=8.9 Hz, 2 H), 7.51 (d, J=8.9 Hz, 2 H), 7.22-7.31 (m, 3 H), 6.87 (s, 1 H), 1.54 (s, 9 H); EI/MS 423 [M]+.

後処理

  1. filtrationfiltered through a pad of Celite®
  2. washThe pad was washed with CHCl3 (20 mL)
  3. additionHeptane (20 mL) was then added to the solution
  4. concentrationthe solution was concentrated under reduced pressure
  5. customThe residue was purified via radial chromatography
  6. customTwo fractions were isolated
  7. customThe first fraction isolated (Rf=0.42)

出典と根拠

ORDレコード
ord-31609f908dfd4ad382c2ce2f2accfb72
出典データセット
uspto-grants-2015_04
特許番号
US09018363B2

反応ノート

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