1-Hydroxybenzotriazole → 5-(5-methyl-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole

HRID 1475185

反応式

HRID 1475185 の反応式
[OH:1][N:2]=[C:3]([NH2:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1.[CH3:16][C:17]1[NH:21][N:20]=[C:19]([C:22](O)=O)[N:18]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:16][C:17]1[NH:21][N:20]=[C:19]([C:22]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[CH:6][C:7]([O:10][C:11]([F:13])([F:12])[F:14])=[CH:8][CH:9]=3)[N:15]=2)[N:18]=1

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27333094-(Trifluoromethoxy)benzamidoximeHCID 206490965-Methyl-1H-1,2,4-triazole-3-carboxylic acid

生成物 1

HCID 867118775-(5-methyl-1H-1,2,4-triazol-3-yl)-3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole収率 37.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N′-hydroxy-4-(trifluoromethoxy)benzimidamide (1.3 g, 5.1 mmol) and 5-methyl-1H-1,2,4-triazole-3-carboxylic acid (650 mg, 5.1 mmol) in DMF (15 mL), EDC.HCl (980 mg, 5.1 mmol) and HOBT (690 mg, 5.1 mmol) were added at RT. The mixture was stirred at RT for 1 h, and then heated to 140° C. for 3 h. The resulting mixture was cooled, diluted with H2O (20 mL) and extracted with EtOAc (4×40 mL). The combined organic layers were washed with H2O (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure, and the residue was purified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% trifluoroacetic acid) to give 5-(5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole as a white solid (590 mg, 37%). MS (ES+) C12H8F3N5O2 requires: 311. found: 312[M+H]+.

後処理

  1. temperatureheated to 140° C. for 3 h
  2. temperatureThe resulting mixture was cooled
  3. extractionextracted with EtOAc (4×40 mL)
  4. washThe combined organic layers were washed with H2O (10 mL) and brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-302b27c651094b56af8061af3d331f9f
出典データセット
uspto-grants-2015_04
特許番号
US09018380B2

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