Dimethyl Sulfoxide → HCID 86597681, 화합물

HRID 1951679노트

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HRID 1951679 반응식
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CS(C)=O.[OH:40][CH2:41][C@@H:42]1[CH2:46][C@@H:45]([OH:47])[CH2:44][NH:43]1>C(OCC)(=O)C>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:43]3[CH2:44][C@H:45]([OH:47])[CH2:46][C@H:42]3[CH2:41][OH:40])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Br:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 15817396(3R,5S)-5-(Hydroxymethyl)pyrrolidin-3-OLHCID 600025592-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-bromo-phenyl)-6-chloro-pyridin-3-yl]-N-methyl-isobutyramide

생성물 1

HCID 86597681HCID 86597681, 화합물수율 48%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

A mixture of 800 mg (1.38 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(2-bromo-phenyl)-6-chloro-pyridin-3-yl]-N-methyl-isobutyramide, 4 ml dimethyl sulfoxide and 1.15 g (6.9 mmol) (2S,4R)-2-(hydroxymethyl)-4-hydroxypyrrolidine was stirred at 130° C. for 24 h. The reaction mixture was cooled to room temperature, diluted with 100 ml ethyl acetate and washed with 200 ml 1 N sodium carbonate solution and 100 ml water. The combined aqueous layers were extracted twice with 100 ml ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated. Purification by flash chromatography gave 434 mg (48%) of the title compound as a yellow foam.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with 200 ml 1 N sodium carbonate solution and 100 ml water
  3. extractionThe combined aqueous layers were extracted twice with 100 ml ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. customevaporated
  6. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-872da50ff4c2497cbc8ef958a54058c9
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404708B2

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