Pyridine → HCID 10088009, compound

HRID 1171034Notes

Reaction equation

HRID 1171034 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[O:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:7][CH:6]=3)=[CH:9][O:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 59794225HCID 59794225, compound

Product 1

HCID 10088009HCID 10088009, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. suspension of Example 13E (74 mg, 0.33 mmol) in dichloromethane (3 mL) was treated with pyridine (0.032 mL, 0.4 mmol) and benzoyl chloride (0.040 mL, 0.34 mmol), stirred at 0° C. for 1 hour, warmed to room temperature, and stirred overnight. The mixture was triturated with hexanes and the precipitate was collected by vacuum filtration, washed with dichloromethane and water, and purified by flash column chromatography on silica gel with ethyl acetate to provide 46 mg (42%) of the desired product. MS (ESI(+)) m/e 331 (M+H)+; 1H NMR (DMSO-d6) δ 10.41 (s, 1H), 8.26 (s, 1H), 7.99-7.94 (m, 5H), 7.62-7.50 (m, 5H), 6.50 (br s, 2H); Anal. Calcd. for C19H14N4O2.0.25H2O: C, 68.15; H, 4.36; N, 16.73. Found: C, 68.20; H, 4.21; N, 19.78.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. customThe mixture was triturated with hexanes
  4. filtrationthe precipitate was collected by vacuum filtration
  5. washwashed with dichloromethane and water
  6. custompurified by flash column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-1e21c5d0deae45da81b952b5dd83e3ed
Source dataset
uspto-grants-2010_11
Patent number
US07829570B2

Reaction notes

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