Diisopropylethylamine → HCID 178461868, Verbindung

HRID 475250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475250
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([Cl:17])=[CH:4][N:3]=1.Cl.O1CCCCC1[N:25]1[C:29]2[CH:30]=[CH:31][C:32]([C@@H:34]([NH2:36])[CH3:35])=[CH:33][C:28]=2[N:27]=[CH:26]1.CCN(C(C)C)C(C)C>CCCCO>[NH:25]1[C:29]2[CH:30]=[CH:31][C:32]([C@@H:34]([NH:36][C:2]3[N:7]=[C:6]([NH:8][C:9]4[CH:13]=[C:12]([CH:14]5[CH2:16][CH2:15]5)[NH:11][N:10]=4)[C:5]([Cl:17])=[CH:4][N:3]=3)[CH3:35])=[CH:33][C:28]=2[N:27]=[CH:26]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 595867992,5-dichloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidin-4-amineHCID 86694728HCID 86694728, Verbindung

Produkt 1

HCID 178461868HCID 178461868, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of 57 (135 mg, 0.5 mmol) in n-BuOH (3 mL) in a microwave vial was added 126 (184 mg, 0.75 mmol), then DIPEA (0.26 mL, 1.5 mmol) was added dropwise. The vial was sealed with a rubber septa and heated in the microwave for 90 min at 160° C. The solvent was evaporated under reduced pressure and the crude residue was taken up in DCM (5 mL) and MeOH (5 mL) and the solvent was again concentrated in vacuo. The residue was diluted in DMF (2 mL) and filtered to remove any undissolved solids. The filtrate was concentrated in vacuo. The residue was purified by reverse phase HPLC to afford 13 mg (6%) of I-46.

Aufarbeitung

  1. customThe vial was sealed with a rubber septa
  2. customThe solvent was evaporated under reduced pressure
  3. concentrationMeOH (5 mL) and the solvent was again concentrated in vacuo
  4. additionThe residue was diluted in DMF (2 mL)
  5. filtrationfiltered
  6. customto remove any undissolved solids
  7. concentrationThe filtrate was concentrated in vacuo
  8. customThe residue was purified by reverse phase HPLC
  9. customto afford 13 mg (6%) of I-46

Quellen und Nachweise

ORD-Eintrag
ord-ef8f328a0d1c4da49779398349c8fc62
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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