ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate → 2-Benzimidazol-2-yl-N-(4-cyano(3-pyridyl))acetamide

HRID 353788

反応式

HRID 353788 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]=1[CH2:20][C:21]([O:23]CC)=O.[NH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:33]#[N:34]>C1COCC1>[N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:11][C:12]=1[CH2:20][C:21]([NH:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:33]#[N:34])=[O:23]

参加物

5

反応物 3

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 2733832Lithium HexamethyldisilazideHCID 106782193-Aminopyridine-4-carbonitrile

生成物 1

HCID 129887822-Benzimidazol-2-yl-N-(4-cyano(3-pyridyl))acetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

LiHMDS (2.5 eq) was added to ethyl 2-benzimidazol-2-ylacetate (1.0 eq) in THF at −78° C. After 1 hour, 3-amino-4-cyanopyridine (0.8 eq) in THF was added. The resulting mixture was allowed to warm to room temperature overnight. The mixture was quenched with NH4Cl (aqueous saturated solution) and extracted with EtOAc. The organic layer washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. The crude material was purified by silica gel chromatography (5:1 EtOAc:hexane) to yield the desired product. LC/MS m/z 278.3 (MH+), Rt 1.88 minutes.

後処理

  1. customThe mixture was quenched with NH4Cl (aqueous saturated solution)
  2. extractionextracted with EtOAc
  3. washThe organic layer washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown solid
  8. customThe crude material was purified by silica gel chromatography (5:1 EtOAc:hexane)

出典と根拠

ORDレコード
ord-9455d186cbdb4ac5ac118dea699b9656
出典データセット
uspto-grants-2004_06
特許番号
US06756383B2

関連ノート

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