1-Butanol → (RS)-6-(3,5-Bis-trifluoromethyl-benzyl)-4-(3,4-dichloro-benzyl)-3-(2-morpholin-4-yl-ethyl)-7,8-dihydro-6H-1,2,3a,6-tetraaza-azulen-5-one

HRID 1281092

Reaktionsgleichung

Reaktionsgleichung von HRID 1281092
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]1[CH2:13][CH2:12][C:11](=S)[NH:10][CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:8]1=[O:24].C(O)CCC.[N:39]1([CH2:45][CH2:46][C:47]([NH:49][NH2:50])=O)[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>>[F:30][C:28]([F:31])([F:29])[C:26]1[CH:25]=[C:5]([CH:4]=[C:3]([C:2]([F:33])([F:32])[F:1])[CH:27]=1)[CH2:6][N:7]1[CH2:13][CH2:12][C:11]2[N:10]([C:47]([CH2:46][CH2:45][N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)=[N:49][N:50]=2)[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:8]1=[O:24]

Komponenten

4

Edukt 3

HCID 2631-ButanolHCID 16784403-(Morpholin-4-yl)propanehydrazideHCID 11421192(RS)-1-(3,5-bis-trifluoromethyl-benzyl)-3-(3,4-dichloro-benzyl)-5-thioxo-[1,4]diazepan-2-one

Produkt 1

HCID 10146213(RS)-6-(3,5-Bis-trifluoromethyl-benzyl)-4-(3,4-dichloro-benzyl)-3-(2-morpholin-4-yl-ethyl)-7,8-dihydro-6H-1,2,3a,6-tetraaza-azulen-5-oneAusbeute 59,2 %

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a solution of 106 mg (0.2 mmol) (RS)-1-(3,5-bis-trifluoromethyl-benzyl)-3-(3,4-dichloro-benzyl)-5-thioxo-[1,4]diazepan-2-one in 1 ml of butan-1-ol 42 mg (0.24 mmol) of 3-morpholin-4-yl-propionic acid hydrazide was added. The reaction mixture was stirred at 130° C. overnight. After evaporation of the solvent in vacuum water (5 ml) was added and the mixture was extracted three times with ethyl acetate. The combined organic layers are dried (MgSO4) and concentrated. The residue was purified by column chromatography (SiO2, dichloromethane/methanol=95:5) to yield 77 mg (59.2%) of the title compound as a light yellow solid. MS m/e (%): 650.0 (M+H+, 100).

Aufarbeitung

  1. customAfter evaporation of the solvent in vacuum water (5 ml)
  2. additionwas added
  3. extractionthe mixture was extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2, dichloromethane/methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-838279cbca694aa3ba4591a7753c8b01
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06452001B2

Verknüpfte Notizen

Wird geladen…