Pyridine → HCID 86664532, compound

HRID 1910726Notes

Reaction equation

HRID 1910726 reaction equation
[C:1](=[O:27])([O:3][C@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[O:17][C:16](=[O:18])[CH:15]=[C:14]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:12]3=2)[NH:7][C@@H:6]([CH3:26])[CH2:5]1)[NH2:2].N1C=CC=CC=1.[C:34](Cl)(=[O:36])[CH3:35]>ClCCl>[C:1](=[O:27])([O:3][C@H:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[O:17][C:16](=[O:18])[CH:15]=[C:14]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:12]3=2)[N:7]([C:34](=[O:36])[CH3:35])[C@@H:6]([CH3:26])[CH2:5]1)[NH2:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86664533HCID 86664533, compound

Product 1

HCID 86664532HCID 86664532, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[Step 3] 226 mg of the cis-benzyl-8-methyl-3-oxo-7,8,9,10-tetrahydro-3H-pyrano[3,2-f]-quinolin-10-yl carbamate and 0.15 mL of pyridine were dissolved in 10 of dichloromethane followed by adding 66 μL of acetyl chloride while cooling with ice and stirring for 1 hour at room temperature. Following completion of the reaction, the solution was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution was added to the resulting residue followed by extracting three times with chloroform. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (ethyl acetate:hexane=1:1) to obtain 250 mg of cis-benzyl-7-acetyl-8-methyl-3-oxo-7,8,9,10-tetrahydro-3H-pyrano[3,2-f]-quinolin-10-yl carbamate in the form of a yellow solid (99%).

Workup

  1. temperaturewhile cooling with ice
  2. customcompletion of the reaction
  3. concentrationthe solution was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution
  4. additionwas added to the resulting residue
  5. extractionby extracting three times with chloroform
  6. washAfter washing with saturated brine
  7. concentrationthe solution was concentrated under reduced pressure
  8. customthe resulting residue was purified

Sources & evidence

ORD record
ord-888e717cc2144243bfd75fed105b5f6d
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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