HCID 18779684, compound → HCID 18779714, compound

HRID 1421760Notes

Reaction equation

HRID 1421760 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]#[N:16])=[CH:5][CH:4]=1.[Cl:17][C:18]1[CH:19]=[CH:20][C:21](=[O:55])[N:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]3[N:32]=[CH:33][N:34](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:35]=3)=[CH:26][N:25]=2)[CH:23]=1>CC#N>[Cl:17][C:18]1[CH:19]=[CH:20][C:21](=[O:55])[N:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][C:31]3[N:32]([CH2:2][C:3]4[CH:8]=[C:7]([C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=5)[C:6]([C:15]#[N:16])=[CH:5][CH:4]=4)[CH:33]=[N:34][CH:35]=3)=[CH:26][N:25]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 18779684HCID 18779684, compoundHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 1

HCID 18779714HCID 18779714, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

5-Bromomethyl-biphenyl-2-carbonitrile from step 4 (51 mg, 0.19 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (100 mg, 0.19 mmol) were dissolved in CH3CN (950 μl) and heated to 60° C. for 14 hours. The solvent was removed in vacuo and th ressidue dissolved in MeOH (950 μl). The reaction mixture was heated to 60° C. for 4 hours. Solvent was removed in vacuo and the residue was purified by flash chromatography [15% MeOH(5 % NH4OH)/CH2Cl2 ] to yield the final product.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionth ressidue dissolved in MeOH (950 μl)
  3. temperatureThe reaction mixture was heated to 60° C. for 4 hours
  4. customSolvent was removed in vacuo
  5. customthe residue was purified by flash chromatography [15% MeOH(5 % NH4OH)/CH2Cl2 ]

Sources & evidence

ORD record
ord-431a6e9496b249c1ad48cd80099059de
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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