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Pyridine → 5-(4-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-3H-[1,3,4]oxadiazol-2-one

HRID 1869287
ノート
印刷プレビュー

反応式

HRID 1869287 の反応式
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][CH2:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([NH:26][NH2:27])=[O:25])=[CH:22][CH:21]=1.N1C=CC=CC=1.[C:36]1([O:42]C(Cl)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>ClCCl.C(OCC)(=O)C>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]2[O:25][C:36](=[O:42])[NH:27][N:26]=2)=[CH:28][CH:29]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 579867444-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzoic Acid Hydrazide

生成物 1

HCID 113054015-(4-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-3H-[1,3,4]oxadiazol-2-one収率 47.1%

試薬・触媒・溶媒

2
HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of: 4-{2-[5-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-benzoic acid hydrazide (Example 4, 276 mg, 0.65 mmol) in dichloromethane (4 mL) add pyridine (104 μL, 1.3 mmol) followed by phenylchloroformate (0.88 μL, 0.71 mmol). Stir the resulting mixture at room temperature until all the starting material is consumed (by TLC analysis). Dilute the mixture with ethyl acetate wash with water then brine dry over MgSO4 and concentrate under reduced pressure. Take the residue up in acetonitrile (5 mL). To this mixture, add DBU (106 μL, 0.71 mmol). Seal the resulting solution; warm it to 170° C. in a Personal Chemistry™ microwave oven and stir at this temperature for 120 min. Cool the reaction to room temperature, dilute with ethyl acetate, wash with 1 M HCl solution (or saturated NaH2PO4 solution) dry over MgSO4 and concentrate. Triturate the resulting residue with dichloromethane several times to give the title compound as a tan solid (137 mg). (recrystallized from ethyl acetate in a sealed tube at 140° C.).

後処理

  1. customis consumed (by TLC analysis)
  2. additionDilute the mixture with ethyl acetate
  3. washwash with water
  4. dry with materialbrine dry over MgSO4
  5. concentrationconcentrate under reduced pressure
  6. customSeal the resulting solution
  7. temperaturewarm it to 170° C. in a Personal Chemistry™ microwave oven
  8. stirringstir at this temperature for 120 min
  9. temperatureCool
  10. customthe reaction to room temperature
  11. washwash with 1 M HCl solution (or saturated NaH2PO4 solution)
  12. dry with materialdry over MgSO4
  13. concentrationconcentrate
  14. customTriturate the resulting residue with dichloromethane several times

出典と根拠

ORDレコード
ord-2239b3638a464ae4a571911ea980236e
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07638539B2

反応ノート

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