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

HRID 1470821노트

반응식

HRID 1470821 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

{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, 2H), 8.00 (d, J=8.9 Hz, 2H), 7.51 (d, J=8.9 Hz, 2H), 7.22-7.31 (m, 3H), 6.87 (s, 1H), 1.54 (s, 9H); EI/MS 423 [M]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f5ef1f9be2484f0fa70a87d556fe02c4
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006468B2

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