Diisopropylethylamine → HCID 123960931, Verbindung

HRID 535550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535550
[NH2:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:4]=1.CCN(C(C)C)C(C)C.[C:34](Cl)(=[O:42])[O:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C(Cl)Cl.CCOCC>[CH:36]1([O:35][C:34](=[O:42])[NH:1][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:13])[N:5]([NH:14][C:15](=[O:24])[CH2:16][C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:4]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 83262Carbonochloridic acid, cyclohexyl esterHCID 70976268HCID 70976268, Verbindung

Produkt 1

HCID 123960931HCID 123960931, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of the product of Example 42 (90 mg, 0.26 mmol), iPr2NEt (0.078 mL, 0.45 mmol), and cyclohexyl carbonochloridate (51.2 mg, 0.315 mmol) in DCM (4 mL) was stirred at room temperature for 8 hours, diluted with Et2O, washed with sat NaHCO3 and brine, dried (MgSO4), filtered, concentrated, and chromatographed (17-25% EtOAc/DCM) to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 11.60 (s, 1H), 8.32 (dd, J=7.8, 1.4 Hz, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.97-8.03 (m, 1H), 7.91 (td, J=7.5, 1.2 Hz, 1H), 7.60-7.65 (m, 1H), 7.41 (s, 4H), 4.47-4.51 (m, 3H), 3.67 (s, 2H), 1.58-1.84 (m, 4H), 1.41-1.54 (m, 1H), 1.10-1.35 (m, 4H); MS (ESI−) M/Z 467 (M−H)−.

Aufarbeitung

  1. washwashed
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (17-25% EtOAc/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-eba5a92365184361befacbb0f49f4848
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859549B2

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