Trifluoroacetic acid → HCID 49854186, compound

HRID 43239Notes

Reaction equation

HRID 43239 reaction equation
[C:1]([O:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:30]=4[Cl:36])[CH2:25][CH2:24]3)[CH:16]=2)[CH2:11][CH2:10][C:9]1=[O:37])(=[O:5])[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1>[C:1]([O:6][CH2:7][N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][N:26]([C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:30]=4[Cl:36])[CH2:25][CH2:24]3)[CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:37])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 49854924(7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)methyl butyrate

Product 1

HCID 49854186HCID 49854186, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of Compound 2B (3.26 g, 5.94 mmol) in THF (100 mL) was added TFA (2.74 mL, 35.63 mmol) followed by DDQ (7.01 g, 30.88 mmol) in THF (40 mL). The reaction was stirred at room temperature over the weekend. The reaction was quenched with water (100 mL) and then poured into water (600 mL) and dichloromethane (100 mL). Solid NaHCO3 (100 g) was added and the mixture stirred for approximately 30 minutes. Dichloromethane (200 mL) was added and the mixture filtered. The collected filtrate was transferred to a separating funnel and the layers separated. The aqueous layer was extracted with dichloromethane (2×100 mL) and the combined organics washed with water (3×100 mL, brine (100 mL) and dried over MgSO4. After filtration, the volatiles were removed. The crude material was purified by silica chromatography eluting 0-4% Methanol/(1:1 ethyl acetate/dichloromethane). The oil was recrystallized from methanol to give Compound 2, (2.03 g, 3.72 mmol, 63% yield). 1H-NMR (300 MHz, CDCl3) δ 7.63 (1H, d), 7.45 (1H, d), 7.19-7.06 (2H, m), 6.99-6.90 (1H, m), 6.88-6.78 (2H, m), 6.52 (1H, d), 6.33 (2H, s), 4.06 (2H, t), 3.17-2.99 (4H, bs), 2.74-2.43 (6H, m), 2.35 (2H, t), 1.94-1.54 (6H, m), 0.93 (3H, t).

Workup

  1. customThe reaction was quenched with water (100 mL)
  2. additionpoured into water (600 mL) and dichloromethane (100 mL)
  3. additionSolid NaHCO3 (100 g) was added
  4. stirringthe mixture stirred for approximately 30 minutes
  5. additionDichloromethane (200 mL) was added
  6. filtrationthe mixture filtered
  7. customThe collected filtrate was transferred to a separating funnel
  8. customthe layers separated
  9. extractionThe aqueous layer was extracted with dichloromethane (2×100 mL)
  10. washthe combined organics washed with water (3×100 mL, brine (100 mL)
  11. dry with materialdried over MgSO4
  12. filtrationAfter filtration
  13. customthe volatiles were removed
  14. customThe crude material was purified by silica chromatography
  15. washeluting 0-4% Methanol/(1:1 ethyl acetate/dichloromethane)
  16. customThe oil was recrystallized from methanol

Sources & evidence

ORD record
ord-e0850a25d6744e2286b4a4ccdd7e72db
Source dataset
uspto-grants-2013_09
Patent number
US08536328B2

Reaction notes

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