Acetonitrile → 5-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-2-methoxy-benzonitrile

HRID 1421770Notes

Reaction equation

HRID 1421770 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1C#N.[Cl:13][C:14]1[CH:15]=[CH:16][C:17](=[O:51])[N:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]3[N:28]=[CH:29][N:30](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:31]=3)=[CH:22][N:21]=2)[CH:19]=1.C[C:53]#[N:54]>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17](=[O:51])[N:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]3[N:28]([CH2:2][C:3]4[CH:4]=[CH:7][C:8]([O:11][CH3:12])=[C:9]([CH:10]=4)[C:53]#[N:54])[CH:29]=[N:30][CH:31]=3)=[CH:22][N:21]=2)[CH:19]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 126680502-(Bromomethyl)-5-methoxybenzonitrileHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 1

HCID 187797965-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-2-methoxy-benzonitrile

Conditions

Temperature
60 °C

Procedure

2-Bromomethyl-5-methoxy-benzonitrile from step 4 (70 mg, 0.30 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (200 mg, 0.378 mmol) were dissolved in CH3CN (2 ml) and heated to 60° C. for 16 hours. The solvent was removed in vacuo and redissolved in MeOH (2 ml). The reaction mixture was heated to 60° C. for several hours. Solvent was removed in vacuo and the resulting residue was purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2 ] to yield the final product.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionredissolved in MeOH (2 ml)
  3. temperatureThe reaction mixture was heated to 60° C. for several hours
  4. customSolvent was removed in vacuo
  5. customthe resulting residue was purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2 ]

Sources & evidence

ORD record
ord-f42466b2aece4cecb109f79883db07a1
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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