2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11476094, compound

HRID 1786308Notes

Reaction equation

HRID 1786308 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([O:15][CH2:16][CH2:17][CH2:18][O:19]CC3C=CC(OC)=CC=3)=[CH:10][C:9]=2[F:29])=[C:6]([CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:5]2[N:37]=[CH:38][N:39]=[C:4]2[N:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl.O>[Cl:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([O:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:10][C:9]=2[F:29])=[C:6]([CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[N:5]2[N:37]=[CH:38][N:39]=[C:4]2[N:3]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86597651HCID 86597651, compound

Product 1

HCID 11476094HCID 11476094, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-7-cycloheptyl-6-(2,6-difluoro-4-{3-[(4-methoxybenzyl)oxy]propoxy}phenyl)[1,2,4]triazolo[1,5-a]pyrimidine (56 mg, 0.1 mmol) in 4 mL of methylene chloride and 0.2 mL of water is added 2,3-dichloro-5,6-dicyano-1,4-bezoquinone (100 mg, 0.44 mmol). The mixture is stirred at room temperature for 20 minutes, then washed with saturated aqueous sodium bicarbonate solution (x2), dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of 33% ethyl acetate in hexanes to 66% ethyl acetate in hexanes. Concentration provides 3-[4-(5-chloro-7-cycloheptyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propan-1-ol as a light yellow solid (34 mg). MS: m/z 437.2 (M+H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (x2)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to a residue
  4. customThe residue is chromatographed over silica gel
  5. washeluting with a gradient of 33% ethyl acetate in hexanes to 66% ethyl acetate in hexanes
  6. concentrationConcentration

Sources & evidence

ORD record
ord-3649847cac1f4e6e99f14d8a98d7a75d
Source dataset
uspto-grants-2009_03
Patent number
US07507739B2

Reaction notes

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