Water → HCID 59472129, Verbindung

HRID 78619

Reaktionsgleichung

Reaktionsgleichung von HRID 78619
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[N:9]=[CH:10][C:11]([C:26]2[CH:36]=[CH:35][C:29]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:28][CH:27]=2)=[N:12][C:13]=1[C:14]1[O:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])=[N:17][N:18]=1.Br[CH2:38][CH3:39].O>CN(C=O)C>[NH2:7][C:8]1[N:9]=[CH:10][C:11]([C:26]2[CH:36]=[CH:35][C:29]([C:30]([N:32]([CH3:34])[CH3:33])=[O:31])=[CH:28][CH:27]=2)=[N:12][C:13]=1[C:14]1[O:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:38][CH3:39])=[N:17][N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 1361172904-[5-amino-6-[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide

Produkt 1

HCID 59472129HCID 59472129, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

Potassium carbonate (25.46 mg, 0.1842 mmol) was added to a mixture of 4-[5-amino-6-[5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide (50 mg, 0.1228 mmol) in DMF (1 mL) at room temperature. Colour change observed from yellow to orange. The resulting suspension was heated at 60-65° C. and bromoethane (14.72 mg, 10.01 μL, 0.1351 mmol) was added slowly. After the addition is complete the reaction heated at 60-65° C. for 30 min. The reaction mixture was cooled to room temperature. Water (2 mL) was added slowly at and the mixture stirred at room temperature for 20 min. A precipitate formed and was filtered and washed with water. The solid was re-dissolved in DCM and dried over MgSO4, filtered and evaporated to dryness. The solid was triturated with acetonitrile to give the product as a yellow solid (38.3 mg, 73% yield); 1H NMR (400.0 MHz, DMSO) d 1.49 (t, 3H), 2.97-3.02 (m, 6H), 4.24-4.29 (m, 2H), 7.17-7.18 (m, 1H), 7.20 (d, 1H), 7.32-7.35 (m, 2H), 7.53 (d, 1H), 7.65 (br s, 2H), 8.05 (d, 1H), 8.17 (d, 2H) and 8.99 (s, 1H) ppm; MS (ES+) 431.24

Aufarbeitung

  1. additionAfter the addition
  2. temperatureheated at 60-65° C. for 30 min
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customA precipitate formed
  5. filtrationwas filtered
  6. washwashed with water
  7. dissolutionThe solid was re-dissolved in DCM
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe solid was triturated with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-869dd47eb181494db9cf6cea0794230a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

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