Trifluoroacetic acid → HCID 178426276, compound

HRID 323648Notes

Reaction equation

HRID 323648 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=O)[C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:24])[C:8]=3[NH:9][C:10]=2[CH:11]=1.FC(F)(F)C(O)=O.[BH4-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=4)[N:13]=[C:12]([OH:24])[C:8]=3[NH:9][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 178426278HCID 178426278, compound

Product 1

HCID 178426276HCID 178426276, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 7-chloro-4-hydroxy-2-(4′-methylphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (495 mg, 1.4 mmol) in tetrahydrofuran (25 mL) was added trifluoroacetic acid (4.5 ml, 58 mmol). The mixture was cooled to 0° C. with an ice bath and sodium borohydride (290 mg, 7.7 mmol) was added. The resulting solution was stirred at 0° C. for 15 minutes, the cooling bath removed, and the reaction mixture was allowed to warm to room temperature. This was then stirred at room temperature for 3 hours after which the reaction was diluted with cold water (65 mL) and stirred for an additional 10 minutes. After this time, the resulting white mixture was extracted with ethyl acetate (120 mL). The organic phase was washed with water (25 mL), brine (25 mL), dried over Na2SO4 and evaporated to dryness. The resulting residue was triturated and filtered twice from warm ethyl acetate/hexane (2:1, 15 mL) and ethyl acetate (6 mL). After drying, this afforded the title compound as a white solid (462 mg, 97%). MP=208-210° C. (d) MS(CI)340(m/e+1) NMR(d6-DMSO): 2.33(s,3H),3.79(s,2H), 6.92(dd,1H,J1=8.1Hz,J2=1.9Hz), 7.11(d,1H,J=8.2 Hz),7.24(app d, 3H), 7.43(d,2H,J=8.2Hz), 9.05(s,1H),11.99(s, 1H);

Workup

  1. customthe cooling bath removed
  2. temperatureto warm to room temperature
  3. stirringThis was then stirred at room temperature for 3 hours after which the reaction
  4. additionwas diluted with cold water (65 mL)
  5. stirringstirred for an additional 10 minutes
  6. extractionAfter this time, the resulting white mixture was extracted with ethyl acetate (120 mL)
  7. washThe organic phase was washed with water (25 mL), brine (25 mL)
  8. dry with materialdried over Na2SO4
  9. customevaporated to dryness
  10. customThe resulting residue was triturated
  11. filtrationfiltered twice
  12. temperaturefrom warm ethyl acetate/hexane (2:1, 15 mL) and ethyl acetate (6 mL)
  13. customAfter drying

Sources & evidence

ORD record
ord-ba3d760a7d7741ec87e3d6de9052c499
Source dataset
uspto-grants-2001_04
Patent number
US06214826B1

Reaction notes

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