Morpholine → HCID 59639516, Verbindung

HRID 556637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556637
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C[Al](C)C.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[N:19]1[C:24]2[N:25]=[C:26]([NH:37][CH2:38][C:39](OC)=[O:40])[N:27]=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[CH3:36])[C:23]=2[CH:22]=[CH:21][C:20]1=[O:43]>ClCCl.CCOC(C)=O>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[N:19]1[C:24]2[N:25]=[C:26]([NH:37][CH2:38][C:39]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[O:40])[N:27]=[C:28]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[CH3:36])[C:23]=2[CH:22]=[CH:21][C:20]1=[O:43]

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 16682925TrimethylaluminumHCID 59639612HCID 59639612, Verbindung

Produkt 1

HCID 59639516HCID 59639516, VerbindungAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under Ar, a soln of morpholine (58 mg, 0.66 mmol) and trimethylaluminum (2M in toluene) (0.33 mL, 0.66 mmol) in dichloromethane was stirred for 10 min. A soln of the product of Example 190 (100 mg, 0.22 mmol) in dichloromethane (2 mL) was added. The resulting mixture was stirred for 16 h, diluted with EtOAc and washed with H2O to give the crude material. Purification by Flash chromatography on silica gel, eluting with EtOAc/hexane/triethylamine (70/30/2, v/v/v), followed by recrystallization from dichloromethane and hexane, gave the desired product (35 mg, 31%). LC-MS: 510.10 (MH+, m/z), 1.96 (Rt, min).

Aufarbeitung

  1. washwashed with H2O
  2. customto give the crude material
  3. customPurification by Flash chromatography on silica gel
  4. washeluting with EtOAc/hexane/triethylamine (70/30/2, v/v/v)
  5. customfollowed by recrystallization from dichloromethane and hexane

Quellen und Nachweise

ORD-Eintrag
ord-c06ffe73dbff4bd393809a7c7b8aa543
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058282B2

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