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

HRID 353788

반응식

HRID 353788 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9455d186cbdb4ac5ac118dea699b9656
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756383B2

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