2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86642115, compound

HRID 1943242Notes

Reaction equation

HRID 1943242 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6](=[O:12])[N:5]3[CH2:13][C@@H:14]([CH2:15][N:16]4[CH2:20][CH2:19][C@@H:18]([CH2:21][NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:17]4)[N:3]1[C:4]=23.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[O:12]=[C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[CH:11][C:2](=[O:1])[N:3]3[C@H:14]([CH2:15][N:16]4[CH2:20][CH2:19][C@@H:18]([CH2:21][NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:17]4)[CH2:13][N:5]1[C:4]=23

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11430Potassium CarbonateHCID 86642114HCID 86642114, compound

Product 1

HCID 86642115HCID 86642115, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a 25 mL round-bottomed flask was added N-[((3S)-1-{[(2R)-4,9-dioxo-1,2,8,9-tetrahydro-4H,7H-imidazo[1,2,3-ij]-1,8-naphthyridin-2-yl]methyl}-3-pyrrolidinyl)methyl]-2,2,2-trifluoroacetamide (240 mg, 0.602 mmol) in 1,4-dioxane (5 ml) at rt under nitrogen to give a orange solution. DDQ (205 mg, 0.904 mmol) was added and the reaction became very dark. The reaction was heated to 80° C. on an oil bath and stirred for 10 h. The reaction was cooled to rt. 5% Aqueous K2CO3 (20 mL) was added and the reaction was extracted with DCM (3×100 mL). The combined organic layers were washed with a saturated aqueous NaCl solution and the organic phase was dried over Na2SO4, filtered and concentrated to give the crude product. The crude product was added to a silica gel column and was eluted with 0-20% MeOH/CHCl3 to give product (85 mg, 0.214 mmol, 35.6% yield) as an orange solid.

Workup

  1. customto give a orange solution
  2. temperatureThe reaction was cooled to rt
  3. extractionthe reaction was extracted with DCM (3×100 mL)
  4. washThe combined organic layers were washed with a saturated aqueous NaCl solution
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product
  9. washwas eluted with 0-20% MeOH/CHCl3

Sources & evidence

ORD record
ord-6806f8bcd6794efd952c30704c16917d
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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