Sodium Carbonate → HCID 44514990、化合物

HRID 1931736ノート

反応式

HRID 1931736 の反応式
[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

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 161288422-Fluoro-4-methylsulfonylphenol2 回HCID 57965012HCID 57965012、化合物2 回

生成物 1

HCID 44514990HCID 44514990、化合物収率 19%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-310b924c655e42a79ae3c1241b1713b7
出典データセット
uspto-grants-2012_05
特許番号
US08188098B2

反応ノート

読み込み中…