4-Methylmorpholine → HCID 131735115, Verbindung

HRID 929301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929301
[Cl:1][C:2]1[C:6]([NH:7][CH3:8])=[CH:5][N:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[N:3]=1.[C:15]([O:19][C:20]([NH:22][C@@H:23]1[CH2:27][CH2:26][C@H:25]([C:28]([OH:30])=O)[CH2:24]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CN1CCOCC1>CN(C=O)C.CCOC(C)=O.O>[C:15]([O:19][C:20](=[O:21])[NH:22][C@@H:23]1[CH2:24][C@H:25]([C:28](=[O:30])[N:7]([C:6]2[C:2]([Cl:1])=[N:3][N:4]([C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[CH:5]=2)[CH3:8])[CH2:26][CH2:27]1)([CH3:16])([CH3:17])[CH3:18]

Komponenten

7

Edukt 3

HCID 79724-MethylmorpholineHCID 1512529(1S,3R)-3-(((tert-butoxy)carbonyl)amino)cyclopentane-1-carboxylic acidHCID 67499849HCID 67499849, Verbindung

Produkt 1

HCID 131735115HCID 131735115, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-chloro-N-methyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (0.109 g, 0.523 mmol) and (1S,3R)-3-((tert-butoxycarbonyl)amino)cyclopentanecarboxylic acid (0.120 g, 0.523 mmol) in DMF (2.09 mL) was added 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyl uronium hexafluorophosphate (HATU, 0.219 g, 0.576 mmol) to give a brown solution. To this solution was added 4-methylmorpholine (0.115 mL, 1.05 mmol). The reaction was stirred at room temperature overnight. The material was diluted with EtOAc and water. The organic layer was dried with MgSO4, filtered and concentrated to give orange oil, which was purified by silica gel chromatography eluting with EtOAc/hexanes provided the title compound F45 as an orange oil (0.100 g, 39%).

Aufarbeitung

  1. customto give a brown solution
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give orange oil, which
  6. customwas purified by silica gel chromatography
  7. washeluting with EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-374a207c7edc495c989cf77efc01d874
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09295260B2

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