Pyridine → HCID 57749427, compound

HRID 1162468Notes

Reaction equation

HRID 1162468 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH2:10])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:17]=1.N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>CN(C1C=CN=CC=1)C.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH:10][C:24](=[O:26])[CH3:25])[N:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:17]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57749423HCID 57749423, compound

Product 1

HCID 57749427HCID 57749427, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 250 mL round-bottomed flask was added 6-bromo-1-(pyridin-2-yl)-1H-benzo[d]imidazol-2-amine (1.00 g, 3.46 mmol), dichloromethane (35 mL), pyridine (0.419 mL, 5.19 mmol), acetic anhydride (0.343 mL, 3.63 mmol) and DMAP (0.0042 g, 0.035 mmol). The mixture was stirred at 25° C. for 2.5 days. The mixture was concentrated and taken up in MeOH/CH2Cl2 and then concentrated onto silica. Purification by silica gel chromatography (0.5 to 4.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a pink solid (0.673 g, 58%). MS (ESI, positive ion) m/z: 331 (M(79Br)+1).

Workup

  1. concentrationThe mixture was concentrated
  2. concentrationconcentrated onto silica
  3. customPurification by silica gel chromatography (0.5 to 4.0% MeOH (2 M in NH3)/CH2Cl2)

Sources & evidence

ORD record
ord-1fece18a65424b63b5987e90fde425c7
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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