Lithium Hexamethyldisilazide → HCID 178507212, compound

HRID 722160Notes

Reaction equation

HRID 722160 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[N:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=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>[NH2:34][C:33]1[C:32]2[C:27](=[CH:28][N:29]=[CH:30][CH:31]=2)[NH:26][C:21](=[O:23])[C:20]=1[C:12]1[NH:13][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[N:11]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 106782193-Aminopyridine-4-carbonitrileHCID 178470772HCID 178470772, compound

Product 1

HCID 178507212HCID 178507212, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiHMDS (3.0 eq) was added to ethyl 3H-imidazo[4,5-b]pyridin-2-ylacetate (1.0 eq) in THF at −78° C. After 20 minutes, a solution of 3-aminopyridine-4-carbonitrile (1.1 eq) in THF was added. The resulting mixture was allowed to warm to room temperature, stirred 3 hours, and then refluxed overnight. The mixture was cooled to 0° C. and quenched with an aqueous saturated NH4Cl solution. A precipitate formed, was filtered off, and was washed repeatedly with ether to yield the desired compound as a brown solid. Purification by reverse phase chromatography afforded the desired product as a yellow solid. LC/MS m/z 279.0 (MH+), Rt 1.29 minutes.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe mixture was cooled to 0° C.
  3. customquenched with an aqueous saturated NH4Cl solution
  4. customA precipitate formed
  5. filtrationwas filtered off
  6. washwas washed repeatedly with ether

Sources & evidence

ORD record
ord-25ac4180e596493a8a2910c52cc11210
Source dataset
uspto-grants-2006_11
Patent number
US07138409B2

Reaction notes

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