2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Toreforant

HRID 76368Notes

Reaction equation

HRID 76368 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].[CH3:11][C:12]1[C:17]([CH:18]=O)=[CH:16][N:15]=[C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[N:13]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(N(CC)CC)C>[OH-].[Na+].ClCCl.CN(C=O)C>[CH3:1][C:2]1[C:3]2[N:10]=[C:18]([C:17]3[C:12]([CH3:11])=[N:13][C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)=[N:15][CH:16]=3)[NH:9][C:4]=2[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

8

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8471TriethylamineHCID 3613321(2-Amino-3,5-dimethylphenyl)amineHCID 462215604-Methyl-2-((3-(1-methylpiperidin-4-yl)propyl)amino)pyrimidine-5-carbaldehyde

Product 1

HCID 23650961Toreforant

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a 4 mL vial were added 3,5-dimethyl-benzene-1,2-diamine.2HCl (69 mg, 0.33 mmol), 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbaldehyde (92 mg, 0.33 mmol), 2,3-dichloro-5,6-dicyano-p-benzoquinone (75 mg, 0.33 mmol), and DMF (2 mL). After addition of triethylamine (0.09 mL, 0.66 mmol), the resultant mixture was stirred for 5 hours at room temperature. The resultant mixture was then diluted with 1N NaOH (7.5 mL) and dichloromethane (7.5 mL). The organic layer was concentrated and purified by flash chromatography to yield the title compound. MS: [M=H]+=393

Workup

  1. concentrationThe organic layer was concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2d742d0f83994f52b66834126fe77f0e
Source dataset
uspto-grants-2014_09
Patent number
US08835633B2

Reaction notes

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