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

반응식

HRID 353802 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-783148e0d98243fbb8fbb1c354743431
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756383B2

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