Dimethyl Sulfoxide → 7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-2-carbonitrile

HRID 17380노트

반응식

HRID 17380 반응식
CS(C)=O.[CH3:5][N:6]([CH3:12])[C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1.F[C:14]1[C:15]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:16]([CH3:33])[C:17](C#N)=[C:18]2[C:22]=1[O:21][C:20]([C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])=[N:19]2.[CH2:40]([N:42](CC)CC)C>[Cl-].[Na+].O>[CH3:5][N:6]([CH3:12])[C@H:7]1[CH2:11][CH2:10][N:9]([C:14]2[C:22]3[O:21][C:20]([C:23]([N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[O:24])([C:40]#[N:42])[NH:19][C:18]=3[CH:17]=[C:16]([CH3:33])[C:15]=2[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:8]1

참가 물질

6

반응물 4

HCID 679Dimethyl Sulfoxide2회HCID 8471TriethylamineHCID 7019156(3S)-(-)-3-(Dimethylamino)pyrrolidineHCID 685850607-Fluoro-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-4-carbonitrile

생성물 1

HCID 685853927-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-2-carbonitrile

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

Under nitrogen atmosphere, a dimethyl sulfoxide (700 μl) solution of (3S)-3-(dimethylamino)pyrrolidine (24 μl, 192 μmol) was added at 150° C. to a dimethyl sulfoxide (2.5 ml) solution of 7-fluoro-5-methyl-6-phenyl-2-(piperidin-1-ylcarbonyl)-1,3-benzoxazole-4-carbonitrile (I-117) (58 mg, 160 μmol) and triethylamine (29 μl, 208 μmol), followed by stirring at the same temperature for 75 minutes. After cooling, saturated brine was added to the reaction liquid, and the reaction liquid was extracted with ethyl acetate. Next, the obtained organic layers were combined, 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 recrystallized from diisopropyl ether/n-hexane to obtain the entitled compound (23 mg, 31%) as a pale yellow solid.

후처리

  1. temperatureAfter cooling
  2. customthe reaction liquid
  3. extractionwas extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cec825b544b24afb86a412823f6cf250
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

반응 노트

불러오는 중…