4-Methylmorpholine → HCID 23289903, Verbindung

HRID 366785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366785
C1C=CC2N(O)N=NC=2C=1.[N:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=O)=[CH:13][CH:12]=1.[Cl:21][C:22]1[CH:42]=[CH:41][C:25]2[CH:26]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[C:27]3[C:32]([CH2:33][S:34][C:24]=2[CH:23]=1)=[CH:31][CH:30]=[CH:29][N:28]=3.CN1CCOCC1>CN(C=O)C.CCOC(C)=O.O>[Cl:21][C:22]1[CH:42]=[CH:41][C:25]2[CH:26]([N:35]3[CH2:36][CH2:37][N:38]([C:18](=[O:20])[CH2:17][C:14]4[CH:13]=[CH:12][N:11]=[CH:16][CH:15]=4)[CH2:39][CH2:40]3)[C:27]3[C:32]([CH2:33][S:34][C:24]=2[CH:23]=1)=[CH:31][CH:30]=[CH:29][N:28]=3

Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 342284-Pyridineacetic acidHCID 757711-HydroxybenzotriazoleHCID 157805018-Chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridine

Produkt 1

HCID 23289903HCID 23289903, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

DEC (464 mg, 2.42 mmol), HOBT (327 mg, 2.42 mmol), and 4-pyridine-acetic acid (332 mg, 2.42 mmol) were added to 1-(8-chloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridin-11-yl)-piperazine (400 mg, 1.21 mmol) and NMM (5.3 ml) in DMF (8 ml), and the mixture was stirred at room temperature for 19 hours. Water (30 ml) and EtOAc (50 ml) were added, and the layers were mixed and separated. The aqueous layer was extracted with EtOAc (3×40 ml). The aqueous layer was basified with saturated NaHCO3 and was extracted with CH2Cl2 (2×20 ml). The organic layers were combined, washed with brine, dried (Na2SO4), decanted and concentrated; the crude product (659 mg) was purified by flash chromatography (30%acetone/CH2Cl2 to 5%MeOH/CH2Cl2) and obtained as a white solid (344 mg, 63%); MS (FAB, M+H)=451; HRMS: calc.: 451.1359; found: 451.1355.

Aufarbeitung

  1. additionthe layers were mixed
  2. customseparated
  3. extractionThe aqueous layer was extracted with EtOAc (3×40 ml)
  4. extractionwas extracted with CH2Cl2 (2×20 ml)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. concentrationconcentrated
  9. customthe crude product (659 mg) was purified by flash chromatography (30%acetone/CH2Cl2 to 5%MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-b1e0f3326cd349119aa8c42037bf25e4
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130229

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