Hydrochloric Acid → HCID 57658324, compound

HRID 1667364Notes

Reaction equation

HRID 1667364 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([O:15][CH:16]3[CH2:25][CH2:24][C:19]4(OCC[O:20]4)[CH2:18][CH2:17]3)=[CH:10][C:9]=2[F:26])[C:6](=[O:27])[CH:5]=[CH:4][C:3]=1[C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1.Cl>O1CCOCC1.O>[NH2:1][C:2]1[N:7]([C:8]2[C:9]([F:26])=[CH:10][C:11]([O:15][CH:16]3[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][CH2:17]3)=[CH:12][C:13]=2[F:14])[C:6](=[O:27])[CH:5]=[CH:4][C:3]=1[C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57658304HCID 57658304, compound

Product 1

HCID 57658324HCID 57658324, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 6-amino-1-[4-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-2,6-difluoro-phenyl]-5-(4-fluorobenzoyl)-1H-pyridin-2-one (0.55 g, 1.10 mmol) in 1,4-dioxane (10 ml) was added 2M aq HCl (5 ml) at room temperature. Stirring was continued for 18 h. Upon completion of reaction the reaction mixture was diluted with water (10 ml) before evaporation of dioxane under reduced pressure. The residual aqueous solution was extracted with EtOAc (2×10 ml). The combined organic layers were dried (Na2SO4), filtered and concentrated to dryness under reduced pressure to give the desired ketone as a white solid (0.43 g, 86%). LCMS purity 98%, m/z 457 [M+H]+, 1H NMR (400 MHz, CDCl3), δ: 2.05-2.15 (2H, m), 2.25-2.45 (4H, m), 2.55-2.70 (2H, m), 4.65-4.75 (1H, m), 5.85 (1H, d), 6.70-6.75 (2H, m), 7.05-7.15 (2H, m), 7.50-7.65 (3H, m),

Workup

  1. customUpon completion of reaction the reaction mixture
  2. extractionThe residual aqueous solution was extracted with EtOAc (2×10 ml)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a9333b227c284232b2650368b0aae94c
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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