1,2-Dichloroethane → HCID 59374187, Verbindung

HRID 473753

Reaktionsgleichung

Reaktionsgleichung von HRID 473753
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[N:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=O)=[CH:10][CH:9]=1.Cl.[CH:25]1([CH2:28][NH2:29])[CH2:27][CH2:26]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH:25]1([CH2:28][NH:29][C:15](=[O:17])[C:14]2[CH:18]=[CH:19][CH:20]=[N:21][C:13]=2[O:12][C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:23][CH:22]=2)[CH2:27][CH2:26]1

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81671(Cyclopropylmethyl)ammonium chlorideHCID 59373922HCID 59373922, Verbindung

Produkt 1

HCID 59374187HCID 59374187, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a 100 mL round-bottomed flask was added 2-(4-(pyridin-2-ylamino)phenoxy)nicotinic acid (0.333 g, 1.08 mmol), cyclopropylmethanamine hydrochloride (0.116 g, 1.08 mmol), and TEA (0.4500 mL, 3.25 mmol) in DMF to stir for 5 min. EDC (0.2314 g, 1.19 mmol) and HOBT (0.1870 g, 1.19 mmol) was then added and allowed to stir overnight. The reaction mixture was diluted with water (10 mL) and extracted with DCM (3×10 mL). The organic extract was washed with water (1×10 mL), saturated sodium chloride (1×10 mL), saturated sodium bicarbonate (1×10 mL), dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage™ pre-packed silica gel column (25M), eluting with a gradient of 1% to 5% methanol in DCM, to provide N-(cyclopropylmethyl)-2-(4-(pyridin-2-ylamino)phenoxy)nicotinamide. MS (ESI, pos. ion) m/z: 361.1 (M+1). IC50 (uM) 0.831.

Aufarbeitung

  1. stirringto stir overnight
  2. extractionextracted with DCM (3×10 mL)
  3. extractionThe organic extract
  4. washwas washed with water (1×10 mL), saturated sodium chloride (1×10 mL), saturated sodium bicarbonate (1×10 mL)
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed through a Biotage™ pre-packed silica gel column (25M)
  9. washeluting with a gradient of 1% to 5% methanol in DCM

Quellen und Nachweise

ORD-Eintrag
ord-e53b9dc0edcb4fcfb370536cba5092d0
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637500B2

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