Lithium Hexamethyldisilazide → HCID 178480638, compound

HRID 353797Notes

Reaction equation

HRID 353797 reaction equation
[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[CH:35]=[N:36][CH:37]=[CH:38][C:39]=1[C:40]#[N:41]>C1COCC1>[NH2:41][C:40]1[C:39]2[C:34](=[CH:35][N:36]=[CH:37][CH:38]=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

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 106782193-Aminopyridine-4-carbonitrileHCID 178470776HCID 178470776, compound

Product 1

HCID 178480638HCID 178480638, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (3.6 eq) was added to ethyl [5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]acetate (1.0 eq) and 3-aminopyridine-4-carbonitrile (1.0 eq) in THF at 0° C. The reaction was stirred overnight. 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 376.3 (MH+), Rt 1.70 minutes.

Workup

  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

Sources & evidence

ORD record
ord-821dfc4cecdf44f0b0fbc8cb948391a0
Source dataset
uspto-grants-2004_06
Patent number
US06756383B2

Reaction notes

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