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

HRID 17385
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 17385
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]([CH3:35])[CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:25])[O:23][C:19]=2[C:18](F)=[C:17]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:16]=1[CH3:43])#[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]([CH3:35])[CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=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:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:16]=1[CH3:43])#[N:14]
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Komponenten

6

Edukt 4

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685850784-cyano-7-fluoro-N,5-dimethyl-6-phenyl-N-(2-phenylethyl)-1,3-benzoxazole-2-carboxamide

Produkt 1

HCID 685848574-cyano-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-N,5-dimethyl-6-phenyl-N-(2-phenylethyl)-1,3-benzoxazole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, a dimethyl sulfoxide (3 ml) solution of (3S)-3-(dimethylamino)pyrrolidine (110 μl, 871 μmol) was added at 150° C. to a dimethyl sulfoxide (12 ml) solution of 4-cyano-7-fluoro-N,5-dimethyl-6-phenyl-N-(2-phenylethyl)-1,3-benzoxazole-2-carboxamide (I-120) (300 mg, 726 μmol) and triethylamine (132 μl, 944 μmol), followed by stirring at the same temperature for 70 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 a crude product of the entitled compound as a solid, and the solid was suspended and washed in diisopropyl ether to obtain the entitled compound (161 mg, 44%) as a pale yellow solid.

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-a24d72036e25496789f93198acff172f
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737166B2

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