1-Hydroxybenzotriazole → 3-(4-(tert-butyl)phenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,2,4-oxadiazole

HRID 1475206

반응식

HRID 1475206 반응식
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([OH:9])=O)[N:3]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[C:32]([C:36]1[CH:45]=[CH:44][C:39]([C:40](=[NH:43])[NH:41]O)=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C.O.CCOC(C)=O>[C:32]([C:36]1[CH:45]=[CH:44][C:39]([C:40]2[N:41]=[C:7]([C:4]3[N:3]=[C:2]([CH3:1])[NH:6][N:5]=3)[O:9][N:43]=2)=[CH:38][CH:37]=1)([CH3:35])([CH3:33])[CH3:34]

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 206490965-Methyl-1H-1,2,4-triazole-3-carboxylic acidHCID 178440936HCID 178440936, 화합물

생성물 1

HCID 867118993-(4-(tert-butyl)phenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,2,4-oxadiazole수율 47.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

5-Methyl-1H-1,2,4-triazole-3-carboxylic acid (200 mg, 1.57 mmol), EDC.HCl (360 mg, 1.89 mmol), and HOBT (255 mg, 1.89 mmol) were dissolved in DMF (15 mL) and the solution was stirred at RT for 30 min. 4-(tert-Butyl)-N-hydroxybenzimidamide (363 mg, 1.89 mmol) was added and the reaction was stirred at RT for 1 h and then at 140° C. for an additional 2 h. The reaction mixture was cooled to RT, and diluted with H2O (100 mL) and EtOAc (100 mL). The organic layer was separated, washed with H2O (2×50 mL) and brine (25 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product which was purified by silica gel chromatography (EtOAc/Hexane 12%-100% EtOAc) to afford 3-(4-(tert-butyl)phenyl)-5-(5-methyl-1H-1,2,4-triazol-3-yl)-1,2,4-oxadiazole as a yellow solid (210 mg, 47%). MS (ES+) C15H17N5O requires: 283. found 284 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.02 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 2.50 (s, 3H), 1.34 (s, 9H).

후처리

  1. stirringthe reaction was stirred at RT for 1 h
  2. waitat 140° C. for an additional 2 h
  3. temperatureThe reaction mixture was cooled to RT
  4. customThe organic layer was separated
  5. washwashed with H2O (2×50 mL) and brine (25 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford the crude product which
  10. customwas purified by silica gel chromatography (EtOAc/Hexane 12%-100% EtOAc)

출처 및 근거

ORD 기록
ord-4a89d5b11a97450fb4609fccd79da53f
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018380B2

연결된 노트

불러오는 중…