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

HRID 2103425
ノート
印刷プレビュー

反応式

HRID 2103425 の反応式
[CH3:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([NH:15][NH2:16])=[O:14])=[CH:11][CH:10]=1.[C:29]1([O:35]C(Cl)=O)C=CC=CC=1.N1C=CC=CC=1.C1CCN2C(=NCCC2)CC1>ClCCl.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][CH:20]=2)[S:5][C:6]=1[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:29](=[O:35])[NH:16][N:15]=2)=[CH:17][CH:18]=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 578043044-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid hydrazide

生成物 1

HCID 116044505-{4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-3H-[1,3,4]oxadiazol-2-one収率 21.5%

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-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzoic acid hydrazide (Example 8, 271 mg, 0.74 mmol) in dichloromethane (7 mL) add phenylchloroformate (94 μL, 0.75 mmol) followed by pyridine (132 μL, 1.63 mmol). Stir the resulting mixture at room temperature until all the starting material is consumed (by TLC analysis). Concentrate the mixture, and then take the residue up in acetonitrile (10 mL). To this mixture, add DBU (220 μL, 1.5 mmol). Seal the resulting solution; warm it to 180° C. in a Personal Chemistry™ microwave oven and stir at this temperature for 15 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 (69 mg).

後処理

  1. customis consumed (by TLC analysis)
  2. concentrationConcentrate the mixture
  3. customSeal the resulting solution
  4. temperaturewarm it to 180° C. in a Personal Chemistry™ microwave oven
  5. stirringstir at this temperature for 15 min
  6. temperatureCool
  7. customthe reaction to room temperature
  8. washwash with 1 M HCl solution (or saturated NaH2PO4 solution)
  9. dry with materialdry over MgSO4
  10. concentrationconcentrate
  11. customTriturate the resulting residue with dichloromethane several times

出典と根拠

ORDレコード
ord-ec916a03ce154a2c8369f331af37f7ed
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576109B2

反応ノート

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