2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 86642094, compound

HRID 1943146Notes

Reaction equation

HRID 1943146 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH:27]4[N:37]5[C:38]6[N:29]([C:30](=[O:40])[CH:31]=[CH:32][C:33]=6[CH2:34][CH2:35][C:36]5=[O:39])[CH2:28]4)[CH2:22][CH2:21]3)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C([O-])(O)=O.[Na+]>O1CCOCC1>[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][N:12]([CH:20]3[CH2:25][CH2:24][N:23]([CH2:26][CH:27]4[N:37]5[C:38]6[N:29]([C:30](=[O:40])[CH:31]=[CH:32][C:33]=6[CH:34]=[CH:35][C:36]5=[O:39])[CH2:28]4)[CH2:22][CH2:21]3)[C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 516892Sodium BicarbonateHCID 86642095HCID 86642095, compound

Product 1

HCID 86642094HCID 86642094, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl){1-[(4,9-dioxo-1,2,8,9-tetrahydro-4H,7H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl)methyl]-4-piperidinyl}carbamate (80 mg, 0.145 mmol) and DDQ (49.4 mg, 0.218 mmol) in 1,4-dioxane (5 ml) was stirred at 120° C. for 2 h. A further 0.5 eq of DDQ (17 mg) was added and the solution stirred for a further 2 h. The mixture was allowed to cool to rt and was treated with sat NaHCO3 (10 ml). The aqueous layer was extracted with 20% MeOH/DCM (3×100 ml). The organic layers were combined, dried MgSO4, filtered and concentrated to afford the crude product (64 mg, 83%).

Workup

  1. extractionThe aqueous layer was extracted with 20% MeOH/DCM (3×100 ml)
  2. filtrationdried MgSO4, filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-259868a8f0ec4971868da2c194b2933a
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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