Acetic Anhydride → HCID 66700094, compound

HRID 1910715Notes

Reaction equation

HRID 1910715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:15]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]([CH3:25])[CH2:16]2)C(=O)C(F)(F)F)=[CH:4][CH:3]=1.C[Si](C)(C)N[Si](C)(C)C.[Na].[O:36]1CC[CH2:38][CH2:37]1.C(OC(=O)C)(=O)C.[Cl-].[NH4+]>O1CCCC1>[C:37]([N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][N:20]=2)[C@H:15]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:16][C@@H:17]1[CH3:25])(=[O:36])[CH3:38]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 25517Ammonium ChlorideHCID 87114732HCID 87114732, compoundHCID 131731074HCID 131731074, compound

Product 1

HCID 66700094HCID 66700094, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

[Step 8] 70 mg of the N-(4-chlorophenyl)-2,2,2-trifluoro-N-[2-methyl-1,2,3,4-tetrahydro-1,8-naphthyridin-4-yl]acetoamide were dissolved in 0.3 mL of tetrahydrofuran followed by the addition of a 1.9 M sodium hexamethyldisilazane/tetrahydrofuran solution at −15° C. After stirring for 30 minutes at −15° C., 45 μL of acetic anhydride were added, and the solution was gradually returned to room temperature followed by stirring for 2 hours. Following completion of the reaction, the solution was neutralized with a saturated aqueous solution of ammonium chloride followed by extracting three times with ethyl acetate. 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=2:1) to obtain 1.5 mg of the target compound in the form of a pale yellow oil (2.5%).

Workup

  1. customwas gradually returned to room temperature
  2. stirringby stirring for 2 hours
  3. customcompletion of the reaction
  4. extractionby extracting three times with ethyl acetate
  5. washAfter washing with saturated brine
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-798bcee16da94461bf24b921902412d3
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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