Isoxazole-5-carbonyl chloride → 4-(4-[Ethyl-[2-(4-methanesulfonyl-phenyl)-1-methylethyl]amino}butyl)-1-(isoxazole-5-carbonyl)-[1,4]diazepan-5-one

HRID 10201

Reaktionsgleichung

Reaktionsgleichung von HRID 10201
Cl.Cl.[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@@H:14]([N:16]([CH2:29][CH2:30]C)[CH2:17][CH2:18][CH2:19][CH2:20][N:21]2[C:27](=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH3:15])=[CH:9][CH:8]=1)(=[O:6])=[O:5].[O:32]1[C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=[N:33]1>C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].O>[CH2:29]([N:16]([CH:14]([CH3:15])[CH2:13][C:10]1[CH:11]=[CH:12][C:7]([S:4]([CH3:3])(=[O:5])=[O:6])=[CH:8][CH:9]=1)[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:27](=[O:28])[CH2:26][CH2:25][N:24]([C:37]([C:36]2[O:32][N:33]=[CH:34][CH:35]=2)=[O:38])[CH2:23][CH2:22]1)[CH3:30]

Komponenten

6

Edukt 2

HCID 2736707Isoxazole-5-carbonyl chlorideHCID 69224426PSD-506 dihydrochloride

Produkt 1

HCID 219784644-(4-[Ethyl-[2-(4-methanesulfonyl-phenyl)-1-methylethyl]amino}butyl)-1-(isoxazole-5-carbonyl)-[1,4]diazepan-5-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

To a mixture of 4-(4-{[(S)-2-(4-methanesulfonylphenyl)-1-methylethyl]-propylamino)butyl)-[1,4]diazepan-5-one dihydrochloride (0.15 g, 0.3 mmole) in toluene (5 mL) and saturated sodium carbonate (2 mL) was added isoxazole-5-carbonyl chloride (0.04 g, 0.31 mmole). The reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride, dried (magnesium sulfate), and concentrated to give 4-(4-[ethyl-[2-(4-methanesulfonyl-phenyl)-1-methylethyl]amino}butyl)-1-(isoxazole-5-carbonyl)-[1,4]diazepan-5-one as a hygroscopic hydrochloride salt (0.14 g) in ethyl acetate/diethyl ether, 316, M+H=505.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated sodium chloride
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3c08ce7580ee47db862cb3ee257c34e1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094778B2

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