Sodium Sulfate → HCID 9841806、化合物

HRID 895515

反応式

HRID 895515 の反応式
C[Al](C)C.[NH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[NH:14][CH2:15][CH2:16][CH3:17])[C:9]#[N:10].CO[C:20](=O)[CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[C:23]1[C:27]1[N:32]=[C:31]([F:33])[CH:30]=[CH:29][CH:28]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl.C(O)(=O)C.O.CO>[CH2:15]([N:14]1[C:13]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=2[N:5]=[C:20]1[CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[C:23]1[C:27]1[N:32]=[C:31]([F:33])[CH:30]=[CH:29][CH:28]=1)[CH2:16][CH3:17]

参加物

9

反応物 4

HCID 24436Sodium SulfateHCID 16682925TrimethylaluminumHCID 223802993-Amino-4-(propylamino)benzonitrileHCID 68499258HCID 68499258、化合物

生成物 1

HCID 9841806HCID 9841806、化合物収率 36.8%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

Trimethylaluminum (0.54 mL of 2.0M in toluene, 1.09mmol) is added dropwise to a solution of 3-Amino-4-propylaminobenzonitrile (152 mg; 0.87 mmol) in dichloromethane (10 mL), and the mixture was stirred at room temperature for 1 hr. A solution of [2-(2-Fluoropyridin-6-yl)-imidazol-1-yl]acetic acid methyl ester (102 mg; 0.43 mmol) in dichloromethane (5 mL) is added all at once, and the mixture heated at reflux for 16 hr. The brown solution is cooled to room temperature and treated dropwise with methanol (1 mL) then water (2 mL) and stirred at room temperature for 15 min. Anhydrous sodium sulfate is added until the gel becomes solid, the mixture is diluted with dichloromethane (100 mL) and filtered through celite. The filtrate is concentrated to give a brown oil which is dissolved in acetic acid (7 mL) and heated at 100° for 72 hr. The mixture is cooled to room temperature and concentrated. The residue is dissolved in ethyl acetate (15 mL), washed with saturated aqueous NaHCO3 (1×50 mL), then brine (1×50 mL), dried (MgSO4), and concentrated, and the residue purified by preparative thin layer chromatography to give 1-n-Propyl-2-{[2-(2-fluoropyrid-6-yl)-1H-imidazol-1-yl]methyl}-5-cyano-1H-benzimidazole as a light brown semi-solid (57 mg).

後処理

  1. temperatureheated
  2. temperatureat reflux for 16 hr
  3. temperatureThe brown solution is cooled to room temperature
  4. filtrationfiltered through celite
  5. concentrationThe filtrate is concentrated
  6. customto give a brown oil which
  7. temperatureheated at 100° for 72 hr
  8. temperatureThe mixture is cooled to room temperature
  9. concentrationconcentrated
  10. dissolutionThe residue is dissolved in ethyl acetate (15 mL)
  11. washwashed with saturated aqueous NaHCO3 (1×50 mL)
  12. dry with materialbrine (1×50 mL), dried (MgSO4)
  13. concentrationconcentrated
  14. customthe residue purified by preparative thin layer chromatography

出典と根拠

ORDレコード
ord-9062e89d56914e4cb5e380926c11f13a
出典データセット
uspto-grants-2005_07
特許番号
US06916819B2

関連ノート

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