1-Hydroxybenzotriazole → N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide

HRID 1978554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978554
Cl.[O:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:15]=[CH:16][C:17]4[S:23](=[O:25])(=[O:24])[CH2:22][CH2:21][C:20]([C:26]([OH:28])=O)=[CH:19][C:18]=4[CH:29]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH2:52]1[CH2:71][O:70][C:54]2([CH2:59][CH2:58][CH:57]([N:60]([CH2:62][C:63]3[CH:69]=[CH:68][C:66]([NH2:67])=[CH:65][CH:64]=3)[CH3:61])[CH2:56][CH2:55]2)[O:53]1>CN(C=O)C.C(N(CC)CC)C>[CH2:71]1[CH2:52][O:53][C:54]2([CH2:55][CH2:56][CH:57]([N:60]([CH2:62][C:63]3[CH:64]=[CH:65][C:66]([NH:67][C:26]([C:20]4[CH2:21][CH2:22][S:23](=[O:24])(=[O:25])[C:17]5[CH:16]=[CH:15][C:14]([C:11]6[CH:12]=[CH:13][C:8]([N:5]7[CH2:6][CH2:7][O:2][CH2:3][CH2:4]7)=[CH:9][CH:10]=6)=[CH:29][C:18]=5[CH:19]=4)=[O:28])=[CH:68][CH:69]=3)[CH3:61])[CH2:58][CH2:59]2)[O:70]1

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10754953HCID 10754953, VerbindungHCID 702434687-(4-Morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid hydrochloride

Produkt 1

HCID 21995695N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamideAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid hydrochloride (200 mg) and 1-hydroxybenzotriazole (0.12 g) in DMF (5 ml) was added at room temperature 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.18 g), and the mixture was stirred for 1 hour. To the mixture was added a solution of 4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]aniline (0.19 g) and triethylamine (0.2 ml) in DMF (3 ml), and the mixture was stirred for 64 hours. The mixture was concentrated under reduced pressure, and to the residue was added water. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with column chromatography (ethanol/ethyl acetate=1:1) to give yellow crystals of N-[4-[N-(4,4-ethylenedioxycyclohexyl)-N-methylaminomethyl]phenyl]-7-(4-morpholinophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxamide (Compound 15) (119 mg).

Aufarbeitung

  1. stirringthe mixture was stirred for 64 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionto the residue was added water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified with column chromatography (ethanol/ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-095303910b82436ea62856cbf4e07e37
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235771B1

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