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

HRID 722163Notes

Reaction equation

HRID 722163 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 178482919HCID 178482919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

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.

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-e0d5dce58fcc4633b3b23dac122b24d8
Source dataset
uspto-grants-2006_11
Patent number
US07138409B2

Reaction notes

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