3-Aminopyridine-2-carbonitrile → HCID 178482919, 화합물

HRID 353799

반응식

HRID 353799 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][N:12]([CH3:33])[CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[CH:32]=[CH:31][C:21]3[NH:22][C:23]([CH2:25][C:26](OCC)=[O:27])=[N:24][C:20]=3[CH:19]=2)[CH2:14]1.[NH2:34][C:35]1[C:36]([C:41]#[N:42])=[N:37][CH:38]=[CH:39][CH:40]=1>C1COCC1>[NH2:42][C:41]1[C:36]2[C:35](=[CH:40][CH:39]=[CH:38][N:37]=2)[NH:34][C:26](=[O:27])[C:25]=1[C:23]1[NH:22][C:21]2[CH:31]=[CH:32][C:18]([N:15]3[CH2:16][CH2:17][CH:13]([N:12]([CH3:11])[CH3:33])[CH2:14]3)=[CH:19][C:20]=2[N:24]=1

참가 물질

5

반응물 3

HCID 5770153-Aminopyridine-2-carbonitrileHCID 2733832Lithium HexamethyldisilazideHCID 178470775HCID 178470775, 화합물

생성물 1

HCID 178482919HCID 178482919, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

LiHMDS (3.6 eq) was added to ethyl {5-[3-(dimethylamino)pyrrolidin-1-yl]-1H-benzimidazol-2-yl}acetate (1.0 eq) and 3-aminopyridine-2-carbonitrile (J. Org. Chem. 1958, 1616-1617; 1.0 eq) in THF at 0° C. The reaction was stirred overnight and then heated at 40° C. for 3 hours. The resulting mixture was quenched with an aqueous saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield a green solid. The crude material was washed successively with CH2Cl2 and MeOH, and then was purified by reverse phase HPLC to provide the desired product. LC/MS m/z 390.2 (MH+), Rt 1.79 minutes.

후처리

  1. customThe resulting mixture was quenched with an aqueous saturated NH4Cl solution
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto yield a green solid
  8. washThe crude material was washed successively with CH2Cl2 and MeOH
  9. customwas purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-cd43ec30d7e04e1f899227dd618d3b4e
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756383B2

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