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 219575ノート

反応式

HRID 219575 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-fd7bcae8767b4dadb5957fe2eb68b033
出典データセット
uspto-grants-2012_06
特許番号
US08202856B2

反応ノート

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