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

HRID 76368
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08835633B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes