Sodium Carbonate → HCID 44514990, 화합물

HRID 1931736노트

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HRID 1931736 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:12].Cl[C:14]1[N:19]=[CH:18][N:17]=[C:16]2[N:20]([CH:23]3[CH2:28][CH2:27][CH:26]([C:29]4[O:33][N:32]=[C:31]([CH:34]([CH3:36])[CH3:35])[N:30]=4)[CH2:25][CH2:24]3)[N:21]=[CH:22][C:15]=12.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][C:14]1[N:19]=[CH:18][N:17]=[C:16]2[N:20]([CH:23]3[CH2:28][CH2:27][CH:26]([C:29]4[O:33][N:32]=[C:31]([CH:34]([CH3:36])[CH3:35])[N:30]=4)[CH2:25][CH2:24]3)[N:21]=[CH:22][C:15]=12

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 161288422-Fluoro-4-methylsulfonylphenol2회HCID 57965012HCID 57965012, 화합물2회

생성물 1

HCID 44514990HCID 44514990, 화합물수율 19%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
160 °C

실험 절차

A mixture of 2-fluoro-4-methanesulfonyl-phenol (Intermediate 1; 66 mg, 0.35 mmol), 4-chloro-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 23; 60 mg, 0.17 mmol) and potassium carbonate (105 mg, 0.76 mmol) in DMF (1.5 mL) was heated in the microwave at 160° C. for 10 min. Saturated aqueous sodium carbonate solution was added to the cooled reaction mixture. The precipitate was filtered, and the filtrate was extracted with ethyl acetate. The extracts were dried (sodium sulfate), filtered, evaporated, and purified by flash chromatography, eluting with 5% methanol/dichloromethane, to give 4-(2-fluoro-4-methanesulfonyl-phenoxy)-1-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidine (16 mg, 19%) as a white solid. Mass spectrum M+=500.9.

후처리

  1. filtrationThe precipitate was filtered
  2. extractionthe filtrate was extracted with ethyl acetate
  3. dry with materialThe extracts were dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography
  7. washeluting with 5% methanol/dichloromethane

출처 및 근거

ORD 기록
ord-310b924c655e42a79ae3c1241b1713b7
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188098B2

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