2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 22142535, compound

HRID 1823587Notes

Reaction equation

HRID 1823587 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.ClC1C=CC=CN=1.ClC1N=C(C2C=CC=CC=2)C(C(OCC)=O)=CC=1.N[C:57]1[N:62]=[C:61]([NH:63][CH2:64][CH2:65][NH:66][C:67]2[CH:72]=[CH:71]C(C3NC=CN=3)=C(C3C=CC(Cl)=CC=3Cl)[N:68]=2)[CH:60]=[CH:59][C:58]=1[N+:86]([O-:88])=[O:87]>CC#N.CCN(C(C)C)C(C)C.C1COCC1.C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:71][CH:72]=[C:67]([NH:66][CH2:65][CH2:64][NH:63][C:61]2[CH:60]=[CH:59][C:58]([N+:86]([O-:88])=[O:87])=[CH:57][N:62]=2)[N:68]=1

Participants

9

Reactant 5

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 79772-ChloropyridineHCID 542007Ethyl 3-(2,4-dichlorophenyl)-3-oxopropanoateHCID 22142808{2-[(6-Amino-5-nitro(2-pyridyl))amino]ethyl}[6-(2,4-dichlorophenyl)-5-imidazolyl(2-pyridyl)]amineHCID 22142863Ethyl 6-chloro-2-phenylpyridine-3-carboxylate

Product 1

HCID 22142535HCID 22142535, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 81531DiisopropylethylamineSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Ethyl 2-(2,4-dichlorophenyl)-6-({2-[(5-nitro(2-pyridyl))amino]ethyl}amino)pyridine-3-carboxylate was prepared from ethyl 3-(2,4-dichlorophenyl)-3-oxopropanoate (ref. Wemple, J.; et. al. Synthesis 1993, 290-292.) as the starting material and THF/ethanol ratio of 3:1 as the solvent in the first step. The oxidation uses DDQ. The final product is achieved directly from the chloropyridine by reacting ethyl 6-chloro-2-phenylpyridine-3-carboxylate with 2-(2-aminoethylamine)-5-nitropyridine in CH3CN and Hünig's base at 120° C. for 18 hours. The procedures are analogous to the general method for {2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}[6-(2,4-dichlorophenyl)-5-imidazolyl(2-pyridyl)]amine.

Workup

  1. customat 120° C.
  2. customfor 18 hours

Sources & evidence

ORD record
ord-6b114c2227e845b788887d9a238b3ad5
Source dataset
uspto-grants-2006_05
Patent number
US07037918B2

Reaction notes

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