3-Aminopyridine-2-carbonitrile → HCID 178480640、化合物

HRID 353800

反応式

HRID 353800 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:11][N:12]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]([O:28]CC)=O)=[N:24][C:20]=3[CH:19]=2)[CH2:14][CH2:13]1.[NH2:33][C:34]1[C:35]([C:40]#[N:41])=[N:36][CH:37]=[CH:38][CH:39]=1>C1COCC1>[NH2:41][C:40]1[C:35]2[C:34](=[CH:39][CH:38]=[CH:37][N:36]=2)[NH:33][C:26](=[O:28])[C:25]=1[C:23]1[NH:22][C:21]2[CH:31]=[CH:32][C:18]([N:15]3[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH2:16]3)=[CH:19][C:20]=2[N:24]=1

参加物

5

反応物 3

HCID 5770153-Aminopyridine-2-carbonitrileHCID 2733832Lithium HexamethyldisilazideHCID 178470776HCID 178470776、化合物

生成物 1

HCID 178480640HCID 178480640、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

LiHMDS (3.6 eq) was added to ethyl [5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetate (1.0 eq) and 3-aminopyridine-2-carbonitrile (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 376.1 (MH+), Rt 1.50 minutes.

後処理

  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

出典と根拠

ORDレコード
ord-0e37607eee534c6a88a584b2dd4318da
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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