2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,1-Dimethylethyl {1-[(4,9-dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl)methyl]-4-piperidinyl}carbamate

HRID 1943140Notes

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[CH:13]([CH2:15][N:16]4[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:17]4)[CH2:14][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:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6](=[O:12])[N:5]3[CH:13]([CH2:15][N:16]4[CH2:17][CH2:18][CH:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:26])[CH3:28])[CH2:20][CH2:21]4)[CH2:14][N:3]1[C:4]=23

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 1,1-dimethylethyl {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 (194 mg, 0.0.483 mmol) (301 mg, 0.694 mmol) in 1,4-dioxane (5 ml) was treated with DDQ (164 mg, 0.724 mmol) and stirred at 60° C. for 24 h. Further DDQ (164 mg, 0.724 mmol) was added and the reaction was stirred for a further 2 h. The reaction was then treated with 5% aqueous potassium carbonate (100 ml), extracted with 20% methanol/DCM (3×200 ml). The organic extracts were dried (MgSO4) and evaporated to give the product as an orange oil (159 mg, 82%).

Workup

stirringthe reaction was stirred for a further 2 h
extractionextracted with 20% methanol/DCM (3×200 ml)
dry with materialThe organic extracts were dried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-02149c6100a44e86b3f2230837ec1aab
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389524B2

Reaction notes

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