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

HRID 2205476Notes

Reaction equation

HRID 2205476 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.

Workup

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

Sources & evidence

ORD record
ord-c3e5fce53e3c4d97a5e4f3f85c089dae
Source dataset
uspto-grants-2016_06
Patent number
US09371311B2

Reaction notes

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