2,5-difluoro-N'-hydroxybenzenecarboximidamide → 5-[1-(2-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-yl]-3-(2,5-difluorophenyl)-1,2,4-oxadiazole

HRID 219575노트

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HRID 219575 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=O)[N:10]=[N:9]1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[C:25](=[N:27]O)[NH2:26]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH3:13])=[C:11]([C:14]2[O:16][N:26]=[C:25]([C:19]3[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=3[F:17])[N:27]=2)[N:10]=[N:9]1

참가 물질

3

반응물 2

HCID 43581602,5-difluoro-N'-hydroxybenzenecarboximidamideHCID 153995471-(2-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid

생성물 1

HCID 596040655-[1-(2-Bromophenyl)-5-methyl-1H-1,2,3-triazole-4-yl]-3-(2,5-difluorophenyl)-1,2,4-oxadiazole

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온도
100 °C

실험 절차

The title compound was prepared following procedure described for Example 1, but starting from 1-(2-bromophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid, prepared according to Zhang, Z.-Y. et al. Magn. Reson. Chem. 1998, 36, 159-460 (56.42 mg; 0.20 mmol) and 2,5-difluoro-N′-hydroxybenzenecarboximid amide (JRD-Fluoro, 37.87 mg; 0.22 mmol). The reaction mixture was filtered through an NH2 SPE column (1 g) and evaporated. The residue was taken up into pyridine and heated at 100° C. for 7 h, in order to complete oxadiazole formation. Pyridine was evaporated and the crude product was purified by flash chromatography (SiO2: 10 g; cyclohexane/EtOAc gradient from 90/10 till 50/50) and dried to afford Example 3 as a yellow solid. 1H NMR: (DMSO-d6, 300 MHz) δ 8.06 (dd, J=1.70 Hz, J=7.73 Hz, 1H), 8.02-7.97 (m, 1H), 7.86 (dd, J=1.89 Hz, J=7.53 Hz, 1H), 7.80-7.69 (m, 2H), 7.63 (dt, J=1.91 Hz, J=6.58 Hz, 2H), 2.61 (s, 3H). LC/MS: 419.93 (M+H)+. HPLC (Method A) Rt 4.92 min (Purity: 96%).

후처리

  1. customprepared
  2. filtrationThe reaction mixture was filtered through an NH2 SPE column (1 g)
  3. customevaporated
  4. customPyridine was evaporated
  5. customthe crude product was purified by flash chromatography (SiO2: 10 g; cyclohexane/EtOAc gradient from 90/10 till 50/50)
  6. customdried

출처 및 근거

ORD 기록
ord-fd7bcae8767b4dadb5957fe2eb68b033
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202856B2

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