1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

HRID 447901ノート

反応式

HRID 447901 の反応式
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]([OH:18])=O)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[N:21]=[C:22]=[N:23]CCCN(C)C.[CH:30]1[CH:31]=[CH:32][C:33]2N(O)N=[N:36][C:34]=2[CH:35]=1.O1CCO[CH2:42][CH2:41]1>>[NH:36]1[C:34]2[C:33](=[CH:32][C:31]([C:22]3[N:23]=[C:16]([C:9]4[S:10][C:11]([C:12]([F:13])([F:14])[F:15])=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:8]=4)[O:18][N:21]=3)=[CH:30][CH:35]=2)[CH:42]=[CH:41]1

参加物

5

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 27833724-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid

生成物 1

HCID 251103463-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole収率 46.7%

実験手順

To a solution of 4-phenyl-5-(trifluoromethyl)-2-thiophenecarboxylic acid in 1,4-dioxane were added under nitrogen atmosphere EDCI (125 mg, 0.65 mmol) and HOBt (88 mg, 0.65 mmol). The reaction was stirred at room temperature for 30 min followed by addition of N′-hydroxyimidamide (114 mg, 0.65 mmol), the reaction was stirred for 30 additional minutes at room temperature followed by 16 h at 95° C. The reaction was concentrated under reduced pressure. The crude was diluted with EtOAc (80 mL) and washed with a saturated solution of NaHCO3 (2×50 ml). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (9:1) to yield 91 mg (46.7%) of the product. MS (EI) m/z: 412 (M+).

後処理

  1. stirringthe reaction was stirred for 30 additional minutes at room temperature
  2. waitfollowed by 16 h at 95° C
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additionThe crude was diluted with EtOAc (80 mL)
  5. washwashed with a saturated solution of NaHCO3 (2×50 ml)
  6. dry with materialThe organic phase was dried over Na2SO4 anhydrous
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by column chromatography

出典と根拠

ORDレコード
ord-3d6dd430590d4c8babf9a29031272426
出典データセット
uspto-grants-2013_07
特許番号
US08481573B2

反応ノート

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