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Dimethyl Sulfoxide → 4-cyano-N-[2-(dimethylamino)-2-oxoethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17391
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17391
CS(C)=O.[CH3:5][N:6]([CH3:12])[C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:26]([CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH3:27])=[O:25])[O:23][C:19]=2[C:18](F)=[C:17]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:16]=1[CH3:41])#[N:14].C(N(CC)CC)C>[Cl-].[Na+].O>[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:26]([CH2:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30])[CH3:27])=[O:25])[O:23][C:19]=2[C:18]([N:9]2[CH2:10][CH2:11][C@H:7]([N:6]([CH3:12])[CH3:5])[CH2:8]2)=[C:17]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:16]=1[CH3:41])#[N:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 68585307HCID 68585307, Verbindung

Produkt 1

HCID 685849564-cyano-N-[2-(dimethylamino)-2-oxoethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamideAusbeute 14,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, a dimethyl sulfoxide (1 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (52 μl, 408 μmol) was added at 150° C. to a dimethyl sulfoxide (6 ml) solution of 4-cyano-N-[2-(dimethylamino)-2-oxoethyl]-7-fluoro-N,5-dimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide (I-125) (134 mg, 340 μmol) and triethylamine (62 μl, 442 μmol), followed by stirring at the same temperature for 50 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (20:1, v/v) gave the entitled compound (24 mg, 14%) as an amorphous substance.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. extractionwas extracted with ethyl acetate
  4. washNext, the combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0bab741dbfa04a6789f2a25b42736215
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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