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4-Methylmorpholine → [4-(2,4-Dimethylphenyl)-[1,4]diazepan-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone

HRID 2411477
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2411477
[O:1]=[S:2]1(=[O:16])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.Cl.[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[N:26]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.CN1CCOCC1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO.O1CCOCC1.O>[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[N:26]1[CH2:32][CH2:31][CH2:30][N:29]([C:11]([C:10]2[CH:9]=[CH:8][C:7]([N:3]3[CH2:4][CH2:5][CH2:6][S:2]3(=[O:1])=[O:16])=[CH:15][CH:14]=2)=[O:13])[CH2:28][CH2:27]1
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Komponenten

8

Edukt 4

HCID 79724-MethylmorpholineHCID 66250114-(1,1-Dioxo-1,2-thiazolidin-2-yl)benzoic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 673808831-(2,4-Dimethylphenyl)-[1,4]diazepane hydrochloride

Produkt 1

HCID 71252897[4-(2,4-Dimethylphenyl)-[1,4]diazepan-1-yl][4-(1,1-dioxo-1lambda6-isothiazolidin-2-yl)phenyl]methanone
Ausbeute 49,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)benzoic acid (253 mg) described in Preparation Example 16, 1-(2,4-dimethylphenyl)-[1,4]diazepane hydrochloride (253 mg) described in Preparation Example 93 and N-methylmorpholine (0.12 mL) was dissolved in a solution of methanol (2 mL), 1,4-dioxane (2 mL) and water (0.5 mL), 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (349 mg) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (223 mg).

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-32da236d9a4e49ac87a05a9c5fd562f3
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08816079B2

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