Sodium Chloride → 4-(5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-ol

HRID 1048933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048933
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])[CH3:2].[CH:17]1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.O[N:39]=[C:40]([C:42]1[C:43]2[CH2:44][CH2:45][CH:46]([OH:51])[C:47]=2[CH:48]=[CH:49][CH:50]=1)[NH2:41].[Na+].[Cl-]>CN(C=O)C>[CH:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[O:9][N:41]=[C:40]([C:42]3[CH:50]=[CH:49][CH:48]=[C:47]4[C:43]=3[CH2:44][CH2:45][CH:46]4[OH:51])[N:39]=2)=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14])([CH3:2])[CH3:17]

Komponenten

7

Edukt 5

HCID 5234Sodium ChlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 235081534-Ethoxy-3-(trifluoromethyl)benzoic acidHCID 75966899N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide

Produkt 1

HCID 251105044-(5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-olAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

In a microwave vial, a stirring solution of 4-ethoxy-3-(trifluoromethyl)benzoic acid (200 mg, 0.97 mmol) in DMF was treated with HOBt (172 mg, 1.26 mmol) and EDCI (242 mg, 1.26 mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of N′,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide (243 mg, 1.26 mmol). The reaction was stirred for additional 30 min at room temperature and then heated to 130° C. for 35 min in the initiator. The reaction was diluted using a saturated solution of NaCl and extracted with EtOAc (80 ml×3). 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 offer the product as pale yellow solid in 63% yield (229 mg).

Aufarbeitung

  1. stirringThe reaction was stirred for additional 30 min at room temperature
  2. additionThe reaction was diluted
  3. extractionextracted with EtOAc (80 ml×3)
  4. dry with materialThe organic phase was dried over Na2SO4 anhydrous
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-13b1020fd6414c388c5363b6ae6e5f7f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382217B2

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