Pyridine → HCID 44548377, compound

HRID 1951592Notes

Reaction equation

HRID 1951592 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:25][C:26]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:27]=1[C:28](Cl)=[O:29]>ClCCl>[Cl:25][C:26]1[CH:34]=[C:33]([Cl:35])[CH:32]=[CH:31][C:27]=1[C:28]([NH:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][CH:9]=2)=[CH:17][CH:16]=1)=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 666452,4-Dichlorobenzoyl chlorideHCID 57465379HCID 57465379, compound

Product 1

HCID 44548377HCID 44548377, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a solution of 4-(2-phenyloxazol-4-yl)benzenamine (299 mg, 1266 μmol) and pyridine (500 μl, 6131 μmol) dissolved in 4 mL dichloromethane at room temperature was added 2,4-dichlorobenzoyl chloride (177 μl, 1266 μmol) all at once. The reaction was stirred at room temperature for 1 hour then concentrated under reduced pressure, taken up in heptane and concentrated again under reduced pressure to afford a yellow solid. The solid was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic extract was dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a yellow solid. The product was purified by preparative reversed phase HPLC. Combination of fractions containing product were concentrated under reduced pressure to afford a colorless solid (100 mg, 19%). ESI+ m/z=409.0 [MH]+.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. concentrationconcentrated again under reduced pressure
  3. customto afford a yellow solid
  4. customThe solid was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure
  9. customto afford a yellow solid
  10. customThe product was purified by preparative reversed phase HPLC
  11. additionCombination of fractions containing product
  12. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-50498b00b6874bce94892262ffcb5bb4
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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