ethyl 2-(1H-1,3-benzodiazol-2-yl)acetate → 4-Amino-5-(1H-benzimidazol-2-yl)thieno[2,3-b]pyridin-6(7H)-one

HRID 353802

反応式

HRID 353802 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][C:21]([O:23]CC)=O.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][C:31]=1[C:32]#[N:33]>C1COCC1>[NH2:33][C:32]1[C:31]2[CH:30]=[CH:29][S:28][C:27]=2[NH:26][C:21](=[O:23])[C:20]=1[C:12]1[NH:11][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=1

参加物

5

反応物 3

HCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 7366072-Aminothiophene-3-carbonitrileHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 1358393724-Amino-5-(1H-benzimidazol-2-yl)thieno[2,3-b]pyridin-6(7H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

LiHMDS (4.3 eq) was added to ethyl 1H-benzimidazol-2-ylacetate (1.1 eq) and 2-aminothiophene-3-carbonitrile (1.0 eq) in THF at 0° C. After 1 hour, the resulting mixture was warmed to room temperature and then stirred overnight. The mixture was quenched with an aqueous saturated NH4Cl solution and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a brown solid. LC/MS m/z 283.1 (MH+), Rt 1.88 minutes.

後処理

  1. customThe mixture was quenched with an aqueous saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a brown solid

出典と根拠

ORDレコード
ord-783148e0d98243fbb8fbb1c354743431
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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