4-Amino-nicotinonitrile → HCID 178507213, compound

HRID 1882895Notes

Reaction equation

HRID 1882895 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[N:11]1([C:17]2[CH:31]=[CH:30][C:20]3[NH:21][C:22]([CH2:24][C:25]([O:27]CC)=O)=[N:23][C:19]=3[CH:18]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[NH2:32][C:33]1[CH:38]=[CH:37][N:36]=[CH:35][C:34]=1[C:39]#[N:40]>C1COCC1>[NH2:40][C:39]1[C:34]2[C:33](=[CH:38][CH:37]=[N:36][CH:35]=2)[NH:32][C:25](=[O:27])[C:24]=1[C:22]1[NH:21][C:20]2[CH:30]=[CH:31][C:17]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)=[CH:18][C:19]=2[N:23]=1

Participants

5

Reactant 3

HCID 5770164-Amino-nicotinonitrileHCID 2733832Lithium HexamethyldisilazideHCID 178470777HCID 178470777, compound

Product 1

HCID 178507213HCID 178507213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (3.3 eq) was added to ethyl (5-morpholin-4-yl-1H-benzimidazol-2-yl)acetate (1.0 eq) and 4-aminopyridine-3-carbonitrile (see J. Chem. Soc. 1967, p1558-1564; 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 brown 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 363.2 (MH+), Rt 1.55 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 brown solid
  8. washThe crude material was washed successively with CH2Cl2 and MeOH
  9. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-de05ba49d3594548a4287133a811747d
Source dataset
uspto-grants-2004_07
Patent number
US06759417B2

Reaction notes

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