1-Hydroxybenzotriazole → 4-{3-[(4'-{[1-Methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl-4-yl)oxy]propyl}morpholine

HRID 1519673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519673
Cl.[CH3:2][NH:3][C:4](=[O:12])[C@H:5](C(=O)OC)[NH:6][CH3:7].[CH3:13]CN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[N:44]1([CH2:50][CH2:51][CH2:52][O:53][C:54]2[CH:59]=[CH:58][C:57]([C:60]3[CH:65]=[CH:64][C:63]([C:66]([OH:68])=O)=[CH:62][CH:61]=3)=[CH:56][CH:55]=2)[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.[C:69](=[O:72])([O-])[OH:70].[Na+]>CN(C=O)C.O>[CH3:13][O:70][C:69](=[O:72])[CH:5]([N:6]([CH3:7])[C:66]([C:63]1[CH:64]=[CH:65][C:60]([C:57]2[CH:56]=[CH:55][C:54]([O:53][CH2:52][CH2:51][CH2:50][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:59][CH:58]=2)=[CH:61][CH:62]=1)=[O:68])[C:4]([NH:3][CH3:2])=[O:12]

Komponenten

9

Edukt 6

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712681444'-[3-(Morpholin-4-yl)propoxy]biphenyl-4-carboxylic acidHCID 86679246N,N2,O-trimethyl-3-oxoserinamide hydrochloride

Produkt 1

HCID 712681684-{3-[(4'-{[1-Methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl-4-yl)oxy]propyl}morpholineAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Intermediate 5-2 (0.24 g), WSC.HCl (0.29 g), HOBt.H2O (0.20 g), and DIPEA (0.27 mL) were added to a DMF (5.0 mL) solution of 4′-[3-(morpholin-4-yl)propoxy]biphenyl-4-carboxylic acid (0.34 g) as obtained in Example 4-(3), and the mixture was stirred for 2 hours at room temperature. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→0/100) to obtain 4-{3-[(4′-{[1-methoxy-3-(methylamino)-1,3-dioxopropan-2-yl](methyl)carbamoyl}biphenyl-4-yl)oxy]propyl}morpholine (colorless oil) (0.11 g, 23%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThen, the desiccant was filtered out
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=50/50→0/100)

Quellen und Nachweise

ORD-Eintrag
ord-a2845a5a32b84e29ad6465a8973c7fcd
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073821B2

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