Pyridine → HCID 44548373, compound

HRID 1951581Notes

Reaction equation

HRID 1951581 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30]>ClCCl>[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:28]=1[C:29]([NH:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[O:6][C:2]([CH3:1])=[C:3]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:4]=2)=[CH:12][CH:11]=1)=[O:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 666452,4-Dichlorobenzoyl chlorideHCID 57465373HCID 57465373, compound

Product 1

HCID 44548373HCID 44548373, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a solution of 4-(5-methyl-4-phenyloxazol-2-yl)benzenamine (311 mg, 1243 μmol) and pyridine, anhydrous (1013 μl, 12425 μmol) in 4 mL dichloromethane at room temperature was added all at once by metered pipet 2,4-dichlorobenzoyl chloride (192 μl, 1367 μmol). The reaction was stirred at room temperature for 1 hour then concentrated under reduced pressure, triturated with heptane and concentrated under reduced pressure. The residue was triturated with ethyl acetate and the isolated solid (170 mg) was purified by reversed phase preparative HPLC. Fractions containing product were combined and concentrated under reduced pressure. The concentrate was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution and the organic separation dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a colorless solid (100 mg, 19%). ESI+ m/z=423.0 [MH]+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customtriturated with heptane
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with ethyl acetate
  5. customthe isolated solid (170 mg) was purified by reversed phase preparative HPLC
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrate was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  9. customthe organic separation
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-1cdc9915277d43a8b4fe1bf55386e754
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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