Dimethylamine, hydrochloride → Ethyl 4-[4-(difluoromethyl)phenoxy]-2-[(dimethylamino)-carbonyl]-1-benzofuran-6-carboxylate

HRID 1177294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177294
[F:1][CH:2]([F:27])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[C:13]3[CH:14]=[C:15]([C:17](O)=[O:18])[O:16][C:12]=3[CH:11]=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[CH:5][CH:4]=1.[CH3:28][N:29](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:30].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNC>CN(C=O)C.O>[F:1][CH:2]([F:27])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[C:13]3[CH:14]=[C:15]([C:17]([N:29]([CH3:30])[CH3:28])=[O:18])[O:16][C:12]=3[CH:11]=[C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:9]=2)=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595601994-[4-(Difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acid

Produkt 1

HCID 59560302Ethyl 4-[4-(difluoromethyl)phenoxy]-2-[(dimethylamino)-carbonyl]-1-benzofuran-6-carboxylateAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-[4-(difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acid (300 mg, 0.80 mmol) in DMF (10 mL) was added HATU (606 mg, 1.59 mmol), DIEA (515 mg, 4.0 mmol) and the solution was stirred at 0° C. for 15 min. Dimethylamine hydrochloride (97.5 mg, 1.20 mmol) was added and the solution was warmed gradually to room temperature and stirred for 14 h. Water was added to the reaction and the product was extracted with CHCl3. The combined organic layers were washed with water twice, dried over MgSO4, and concentrated. The product was purified via gradient silica gel chromatography using CHCl3/MeOH (100/0 to 95/5) to give the title compound (240 mg, 70%) as a light yellow solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.38 (t, J=7.16 Hz, 3 H) 3.13 (s, 3 H) 3.32 (s, 3 H) 4.38 (q, J=7.16 Hz, 2 H) 6.64 (t, J=56.61 Hz, 1 H) 7.09 (d, J=8.48 Hz, 2 H) 7.16 (s, 1 H) 7.50 (d, J=8.48 Hz, 2 H) 7.55 (s, 1 H) 8.05 (s, 1 H).

Aufarbeitung

  1. temperaturethe solution was warmed gradually to room temperature
  2. stirringstirred for 14 h
  3. extractionthe product was extracted with CHCl3
  4. washThe combined organic layers were washed with water twice
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe product was purified via gradient silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-53fcd05ac7624cffb5977de6e25088f8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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