1-Butanol → HCID 178461872, Verbindung

HRID 475220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475220
Cl.O1CCCCC1[N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C@@H:17]([NH2:19])[CH3:18])=[CH:16][C:11]=2[N:10]=[CH:9]1.Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[NH:32][N:31]=[C:30]([CH:33]3[CH2:35][CH2:34]3)[CH:29]=2)[CH:24]=[CH:23][N:22]=1.CCCCO.CCN(C(C)C)C(C)C>CCOC(C)=O.CO.O>[NH:8]1[C:12]2[CH:13]=[CH:14][C:15]([C@@H:17]([NH:19][C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:29]=[C:30]([CH:33]5[CH2:35][CH2:34]5)[NH:31][N:32]=4)[CH:24]=[CH:23][N:22]=3)[CH3:18])=[CH:16][C:11]=2[N:10]=[CH:9]1

Komponenten

8

Edukt 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 86694728HCID 86694728, VerbindungHCID 178478345HCID 178478345, Verbindung

Produkt 1

HCID 178461872HCID 178461872, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A 5 mL microwave tube was charged with 126 (208.2 mg, 0.85 mmol), 53 (100 mg, 0.42 mmol) and n-BuOH (1.2 mL) then DIPEA (0.371 mL) was added, the tube sealed and heated to 140° C. for 18 h in an oil bath. The reaction cooled and diluted with EtOAc (50 mL). Water (25 mL) and some MeOH (1 mL) were added and the phases were separated. The organic layer was washed with brine (25 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by HPLC and SFC to afford 34.4 mg (22%) of I-5 as a white solid: SFC RT=0.72 min.

Aufarbeitung

  1. customthe tube sealed
  2. temperatureThe reaction cooled
  3. customthe phases were separated
  4. washThe organic layer was washed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by HPLC and SFC
  9. customto afford 34.4 mg (22%) of I-5 as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-46d0bb890f4a419f95b06bd43643b7ce
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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