1,2-Dichloroethane → HCID 56597704, Verbindung

HRID 1522357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1522357
[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, 2 H), 0.94 (dd, J=8.34, 2.27 Hz, 2 H), 1.57 (d, J=6.57 Hz, 6 H), 2.12 (s, 3 H), 2.13-2.18 (m, 1 H), 4.62 (d, J=4.80 Hz, 2 H), 5.38 (s, 1 H), 5.54 (s, 1 H), 8.37 (s, 1 H), 8.44-8.54 (m, 3 H), 8.91 (d, J=6.06 Hz, 2 H), 9.04 (s, 1 H), 11.51 (br. s., 1 H).

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-e921c5f136e24e238cb26036e07da07e
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073924B2

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