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

HRID 17378

Reaktionsgleichung

Reaktionsgleichung von HRID 17378
[CH3:1]S(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]([CH3:33])N3C=CC=CC3)=[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:44]([CH2:47][CH3:48])[CH2:45][CH3:46])C>[Cl-].[Na+].O>[C:13]([C:15]1[C:20]2[N:21]=[C:22]([C:24]([N:26]([CH3:33])[C:47]3[CH:48]=[CH:1][CH:46]=[CH:45][N:44]=3)=[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:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:16]=1[CH3:41])#[N:14]

Komponenten

6

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 685843394-cyano-7-fluoro-N,5-dimethyl-6-phenyl-N-pyridin-1-yl-1,3-benzoxazole-2-carboxamide

Produkt 1

HCID 685854824-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-N-pyridin-2-yl-1,3-benzoxazole-2-carboxamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, a dimethyl sulfoxide (2 ml) solution of (3R)-3-(dimethylamino)pyrrolidine (74 μl, 581 μmol) was added at 150° C. to a dimethyl sulfoxide (17 ml) solution of 4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-N-pyridin-1-yl-1,3-benzoxazole-2-carboxamide (I-116) (187 mg, 484 μmmol) and triethylamine (88 μl, 629 μmol), followed by stirring at the same temperature for 3 hours. 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 (47 mg, 20%) 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-e5ba5f37631a4c88bf085887bae8b6ae
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737166B2

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