Methylamine → HCID 68319533、化合物

HRID 1966763ノート

反応式

HRID 1966763 の反応式
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][NH2:8].[Br:9][C:10]1[CH:32]=[CH:31][C:13]2[N:14]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:15]([C:17]3[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=3[C:19]([NH:21]O)=[NH:20])=[N:16][C:12]=2[CH:11]=1>C1COCC1.N1C=CC=CC=1>[CH3:7][NH:8][C:2]([C:1]1[O:5][N:21]=[C:19]([C:18]2[CH:23]=[CH:24][CH:25]=[CH:26][C:17]=2[C:15]2[N:14]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:13]3[CH:31]=[CH:32][C:10]([Br:9])=[CH:11][C:12]=3[N:16]=2)[N:20]=1)=[O:3]

参加物

6

反応物 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 178448432HCID 178448432、化合物

生成物 1

HCID 68319533HCID 68319533、化合物収率 37%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To a solution of oxalyl chloride (0.17 mL, 1.99 mmol) in anhydrous THF (20 mL) is added methylamine 2.0M in THF (0.99 mL, 1.99 mmol) at 0° C. The solution is stirred at 0° C. to room temperature for 0.5 hours and added to a stirred solution of 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-N-hydroxy-benzamidine (350 mg, 0.9 mmol) in anhydrous pyridine (5 mL). The reaction mixture is stirred at room temperature for 1 hour and then heated to 50° C. and stirred for 16 hours. The reaction mixture is cooled to room temperature and concentrated in vacuo. Dichloromethane is added and the organics washed sequentially with saturated NaHCO3 (20 mL) solution and H2O (20 mL) then dried (Na2SO4), filtered and concentrated. Purification via flash chromatography (25 g silica gel, 50-60% EtOAc/heptane) affords 3-[2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-phenyl]-[1,2,4]oxadiazole-5-carboxylic acid methylamide (150 mg, 37%)

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 1 hour
  2. stirringstirred for 16 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. additionDichloromethane is added
  6. washthe organics washed sequentially with saturated NaHCO3 (20 mL) solution and H2O (20 mL)
  7. dry with materialthen dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification via flash chromatography (25 g silica gel, 50-60% EtOAc/heptane)

出典と根拠

ORDレコード
ord-cb84843541094ddea8f9a82bf5e7003a
出典データセット
uspto-grants-2013_04
特許番号
US08420655B2

反応ノート

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