2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11515495, compound

HRID 1371567Notes

Reaction equation

HRID 1371567 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]1[C:20]1[C:21]([NH2:25])=[N:22][O:23][N:24]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]=[C:10]1[C:20]1[C:21]([NH2:25])=[N:22][O:23][N:24]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21071297HCID 21071297, compound

Product 1

HCID 11515495HCID 11515495, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4,5-dihydro-1-(2-methoxyphenyl)-4-phenyl-1H-imidazol-2-yl)-1,2,5-oxadiazol-3-amine (34 mg, 0.10 mmol) was dissolved in THF with DDQ (23 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 2 hours, filtered through silica and resubjected to the same reaction conditions overnight. The reaction mixture was absorbed onto a Biotage column and eluted with 5 to 30% EtOAc/hexanes to give a white foam, 28 mg, 0.084 mmol, 84%. HPLC Method B Rt 4.50 min, MH+ 334.10. 1H NMR (500 MHz, CDCl3) δ 7.76 (m, 2H), 7.42 (m, 1H), 7.35 (m, 2H), 7.23 (m, 2H), 7.00 (m, 2H), 5.71 (s, 2H), 3.64 (s, 3H).

Workup

  1. filtrationfiltered through silica
  2. customresubjected to the same reaction conditions overnight
  3. customThe reaction mixture was absorbed onto a Biotage column
  4. washeluted with 5 to 30% EtOAc/hexanes
  5. customto give a white foam, 28 mg, 0.084 mmol, 84%

Sources & evidence

ORD record
ord-09ae2af740444a1781f6741b4a6cc6a8
Source dataset
uspto-grants-2007_01
Patent number
US07157476B2

Reaction notes

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