Methyl Ethyl Ketone → HCID 13078390, 화합물

HRID 223256

반응식

HRID 223256 반응식
C1(S(CC[CH2:12][C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)(=O)=O)C=CC=CC=1.Cl.[F:23][C:24]1[CH:38]=[CH:37][C:27]2[C:28]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[N:29][O:30][C:26]=2[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:45][C:46](=O)[CH2:47]C>O>[F:23][C:24]1[CH:38]=[CH:37][C:27]2[C:28]([CH:31]3[CH2:32][CH2:33][N:34]([CH2:45][CH2:46][CH2:47][C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[NH:14][C:13]=4[CH3:12])[CH2:35][CH2:36]3)=[N:29][O:30][C:26]=2[CH:25]=1

참가 물질

6

반응물 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochlorideHCID 86738585HCID 86738585, 화합물

생성물 1

HCID 13078390HCID 13078390, 화합물수율 31.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A stirred mixture of 3.1 g of 2-methyl-3-(3-phenylsulfonylpropylindole, 2.1 g of 6-fluoro-3-(4-piperidyl)-1,2-benzisoxazole hydrochloride, 6.3 g of potassium carbonate and 50 ml of 2-butanone was heated under reflux for 24 hrs. The reaction mixture was poured into water and the aqueous mixture was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The resultant oil was triturated with isopropyl ether and the solid was collected. The solid was combined with a 1.6 g sample of previously prepared material and the combined sample was chromatographed on 100 g silica gel, using 2% methanol-chloroform as eluent. The eluent was evaporated and the solid was dissolved in 125 ml toluene and a saturated hydrogen chloride-toluene solution was added until no more precipitate formed. The precipitate was filtered and dried. Recrystallization from acetone afforded 2.7 g (31.5%) of product, mp 208°-210°.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hrs
  3. extractionthe aqueous mixture was extracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe resultant oil was triturated with isopropyl ether
  9. customthe solid was collected
  10. customthe combined sample was chromatographed on 100 g silica gel
  11. customThe eluent was evaporated
  12. dissolutionthe solid was dissolved in 125 ml toluene
  13. additiona saturated hydrogen chloride-toluene solution was added until no more precipitate
  14. customformed
  15. filtrationThe precipitate was filtered
  16. customdried
  17. customRecrystallization from acetone

출처 및 근거

ORD 기록
ord-a5cf6dc182724d0092a082dcdc708b27
출처 데이터셋
uspto-grants-1982_10
특허 번호
US04352811

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