Potassium Carbonate → HCID 44241710, 화합물

HRID 1951681노트

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HRID 1951681 반응식
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[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][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[OH:43][CH2:44][C@@H:45]1[C@@H:49]([OH:50])[CH2:48][CH2:47][NH:46]1>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([CH3:34])([CH3:33])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:46]3[CH2:47][CH2:48][C@H:49]([OH:50])[C@H:45]3[CH2:44][OH:43])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 11073391(2R,3S)-2-(hydroxymethyl)pyrrolidin-3-olHCID 235027842-(3,5-Bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(4-fluoro-2-methylphenyl)pyrid-3-yl)-N,2-dimethylpropanamide

생성물 1

HCID 44241710HCID 44241710, 화합물수율 67.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

A mixture of 11.0 g (20.6 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide, 14.3 g (103 mmol) potassium carbonate and 12.2 g (75.7 mmol) (2R,3S)-2-(hydroxymethyl)-3-hydroxypyrrolidine in 110 ml dimethyl sulfoxide was stirred at 130° C. for 68 h. The reaction mixture was diluted with 800 ml ethyl acetate and washed with 800 ml saturated sodium carbonate solution, 500 ml water and 750 ml brine. The combined aqueous layers were extracted with two 800-ml portions of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography gave 8.48 g (67%) of the title compound as a light yellow foam.

후처리

  1. washwashed with 800 ml saturated sodium carbonate solution, 500 ml water and 750 ml brine
  2. extractionThe combined aqueous layers were extracted with two 800-ml portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-5e5aa29e9f3c4269919cd225fc294745
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404708B2

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