1,2-Dichloroethane → HCID 56597704, Verbindung

HRID 475965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475965
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=[C:12]([C:13]([OH:15])=O)[C:7]=2[CH:6]=[N:5]1)[CH3:3].[NH2:22][CH2:23][C:24]1[C:25](=[O:34])[NH:26][C:27]([CH3:33])=[CH:28][C:29]=1[CH:30]1[CH2:32][CH2:31]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[CH:30]1([C:29]2[CH:28]=[C:27]([CH3:33])[NH:26][C:25](=[O:34])[C:24]=2[CH2:23][NH:22][C:13]([C:12]2[C:7]3[CH:6]=[N:5][N:4]([CH:2]([CH3:1])[CH3:3])[C:8]=3[N:9]=[C:10]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:11]=2)=[O:15])[CH2:31][CH2:32]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 201146251-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidHCID 671242083-(Aminomethyl)-4-cyclopropyl-6-methyl-2(1H)-pyridinone

Produkt 1

HCID 56597704HCID 56597704, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (100 mg, 0.354 mmol), 3-(aminomethyl)-4-cyclopropyl-6-methyl-2(1H)-pyridinone (104 mg, 0.354 mmol), EDC (81 mg, 0.425 mmol), HOAt (48 mg, 0.354 mmol), and N-methylmorpholine (0.156 mL, 1.42 mmol) were suspended in DMF (5 mL) and stirred at room temperature overnight. The contents were filtered, washed with ethanol, and then concentrated in vacuo. The crude solid was purified by reverse phase HPLC (mobile phase: 20-40%, ACN in H2O, 0.1% TFA). The isolated solid was then neutralized with saturated NaHCO3, and washed with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound as an off-white solid, 0.042 g (26%). LCMS E-S (M+H)=443.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.71-0.78 (m, 2H), 0.94 (dd, J=8.34, 2.27 Hz, 2H), 1.57 (d, J=6.57 Hz, 6H), 2.12 (s, 3H), 2.13-2.18 (m, 1H), 4.62 (d, J=4.80 Hz, 2H), 5.38 (s, 1H), 5.54 (s, 1H), 8.37 (s, 1H), 8.44-8.54 (m, 3H), 8.91 (d, J=6.06 Hz, 2H), 9.04 (s, 1H), 11.51 (br. s., 1H).

Aufarbeitung

  1. filtrationThe contents were filtered
  2. washwashed with ethanol
  3. concentrationconcentrated in vacuo
  4. customThe crude solid was purified by reverse phase HPLC (mobile phase: 20-40%, ACN in H2O, 0.1% TFA)
  5. washwashed with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c44f7cb1b5a449a19b2f3011ec46279f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637509B2

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