Pyridine → HCID 16678748, compound

HRID 1455612Notes

Reaction equation

HRID 1455612 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)(Cl)=O.[C:18]1([C:24]2[N:29]=[C:28]([NH2:30])[CH:27]=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CC=CC=1>CN(C)C=O>[N:1]1([CH2:10][C:11]([NH:30][C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:29]=2)=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 5984302-Amino-6-phenylpyridineHCID 805645Benzoimidazol-1-yl-acetic acid

Product 1

HCID 16678748HCID 16678748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1H-benzimidazol-1-yl)acetic acid (1 g, 5.68 mmol) (Example 1B) in N,N-dimethylformamide (25 mL) was added thionyl chloride (0.4 mL, 5.56 mmol) drop-wise and the reaction mixture stirred at room temperature for 1 h. 6-Phenyl-pyridin-2-ylamine (5.46 mmol) and pyridine (4 mL) were then added to the reaction mixture and stirred at room temperature for 17 h. The reaction mixture was then concentrated in vacuo and dichloromethane was added and transferred to a separating funnel where the organics were washed with 0.1M hydrochloric acid and 10% ammonium hydroxide solution. The organic layers were combined and washed with saturated aqueous sodium chloride, dried (Mg2SO4), filtered and concentrated in vacuo. The residue was then purified by column chromatography using silica and eluting with 0-10% methanol in dichloromethane, affording the title compound. 1H NMR (400 MHz, CD3OD) δ ppm 5.29 (2H, s), 7.28-7.35 (2H, m), 7.39-7.48 (3H, m), 7.54 (1H, d, J=7.2 Hz), 7.62 (1H, d, J=7.7 Hz), 7.71 (1H, d, J=7.3 Hz), 7.81 (1H, t, J=7.9 Hz), 7.98 (1H, br d), 8.05 (2H, d, J=7.3 Hz), 8.23 (1H, s). MS (ES) m/z: 329.1 [M+H].

Workup

  1. stirringstirred at room temperature for 17 h
  2. concentrationThe reaction mixture was then concentrated in vacuo and dichloromethane
  3. additionwas added
  4. customtransferred to a separating funnel
  5. washwhere the organics were washed with 0.1M hydrochloric acid and 10% ammonium hydroxide solution
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried (Mg2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was then purified by column chromatography
  11. washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-d0ac5a6c56ee4fff943df1eb4a037210
Source dataset
uspto-grants-2009_01
Patent number
US07482469B2

Reaction notes

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