2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59716583, compound

HRID 2224291Notes

Reaction equation

HRID 2224291 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:31](=[O:32])[N:11]3[NH:12][CH:13]([CH3:30])[C:14]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)=[C:15]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)[C:10]3=[N:9]2)=[CH:5][CH:4]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[F:35][C:2]([F:1])([F:36])[C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]2[C:31](=[O:32])[N:11]3[N:12]=[C:13]([CH3:30])[C:14]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)=[C:15]([C:16]4[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=4)[C:10]3=[N:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59716562HCID 59716562, compound

Product 1

HCID 59716583HCID 59716583, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(trifluoromethyl)benzyl)-7,8-bis(4-chlorophenyl)-6-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (28 mg, 0.053 mmol), prepared as described in Example 469 in CH2Cl2 (0.5 mL) at RT was added DDQ (15 mg, 0.064 mmol). The reaction was stirred at RT for 1 h. LC-MS showed the completion of the reaction. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by using silica gel column chromatography using an automated system eluting with a gradient of (0% to 80% EtOAc for 20 min.) to give the title compound, 2-(4-(trifluoromethyl)benzyl)-7,8-bis(4-chlorophenyl)-6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (23 mg, 84% yield) as a yellow solid in 84% yield. HPLC retention time: 4.18 min; MS [M+H]+: found 529. 1H NMR (CDCl3, 400 MHz) δ 7.61 (d, 2H), 7.52 (d, 2H), 7.35 (dd, 2H), 7.27 (dd, 2H), 7.16 (dd, 2H), 7.02 (dd, 2H), 5.28 (s, 2H), 2.29 (s, 3H).

Workup

  1. customthe completion of the reaction
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe resulting residue was purified
  4. washeluting with a gradient of (0% to 80% EtOAc for 20 min.)

Sources & evidence

ORD record
ord-f5d05a89ba554b67978ce727bf573c17
Source dataset
uspto-grants-2008_05
Patent number
US07378418B2

Reaction notes

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