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4-Methylmorpholine → (Rac)-(3-diethylamino-pyrrolidin-1-yl)-[2-(3-hexyl-phenyl)-5-iodo-3-methyl-3h-imidazol-4-yl]-methanone

HRID 545366
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 545366
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:17]([CH3:18])[C:16]([C:19]([OH:21])=O)=[C:15]([I:22])[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[CH2:41]([N:43]([CH2:49][CH3:50])[CH:44]1[CH2:48][CH2:47][NH:46][CH2:45]1)[CH3:42]>CC#N>[CH2:41]([N:43]([CH2:49][CH3:50])[CH:44]1[CH2:48][CH2:47][N:46]([C:19]([C:16]2[N:17]([CH3:18])[C:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=3)=[N:14][C:15]=2[I:22])=[O:21])[CH2:45]1)[CH3:42]
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Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 199619953-(Diethylamino)pyrrolidineHCID 671332392-(3-Hexyl-phenyl)-5-iodo-3-methyl-3H-imidazole-4-carboxylic acid2×

Produkt 1

HCID 57541119(Rac)-(3-diethylamino-pyrrolidin-1-yl)-[2-(3-hexyl-phenyl)-5-iodo-3-methyl-3h-imidazol-4-yl]-methanone
Ausbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 0.41 g (1.0 mmol) of 2-(3-hexyl-phenyl)-5-iodo-3-methyl-3H-imidazol-4-carboxylic acid (intermediate 1) in 10 ml of MeCN was treated with 0.192 g (1.1 mmol) of 2-chloro-4,6-dimethoxy-[1,3,5]triazine and cooled down to 0° C. 0.33 ml=0.30 g (3.0 mmol) of N-methylmorpholine was added and stirring continued at 0° C. for another 2 hours. Then, a solution of 0.159 g (1.1 mmol) of (rac)-diethyl-pyrrolidin-3-yl-amine in 5 ml of MeCN was added and the reaction mixture was allowed the reach RT. After stirring at RT for 18 hours, it was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.39 g (73%) of the title compound as light brown oil. MS: 537.3 (MH+).

Aufarbeitung

  1. customthe reach RT
  2. stirringAfter stirring at RT for 18 hours
  3. additionit was poured
  4. extractionextracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-acf2627b64804c768efe36e784304fb2
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935707B2

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