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Triazabicyclodecene → 3-Amino-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

HRID 335324
Notes
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Reaction equation

HRID 335324 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7]C)=O.N1CCCN2CCCN=C12.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH2:36][NH2:37])[CH2:26][CH2:25]1>C1(C)C=CC=CC=1.CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([NH:37][CH2:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[N:27]1[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]1)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 79873TriazabicyclodeceneHCID 337778Methyl 3-amino-4-methylbenzoateHCID 27955682-(4-Methyl-1-piperazinyl)benzenemethanamine

Product 1

HCID 866956843-Amino-4-methyl-N-(2-(4-methylpiperazin-1-yl)benzyl)benzamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

A solution of methyl 3-amino-4-methylbenzoate (commercially available) (1.609 g, 9.74 mmol), TBD (2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine) (0.678 g, 4.87 mmol) and (2-(4-methylpiperazin-1-yl)phenyl)methanamine (commercially available) (2 g, 9.74 mmol) in toluene (30 ml) was heated at reflux overnight. The reaction mixture was diluted with EtOAc and washed with sat.NaHCO3 and water. The organic portion was separated, dried (MgSO4) and concentrated in vacuo. The product was purified by chromagraphy on silica eluting with a gradient of 0-20% 2M NH3 in MeOH/DCM to afford the title compound;

Workup

  1. temperatureat reflux overnight
  2. washwashed
  3. customThe organic portion was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by chromagraphy on silica eluting with a gradient of 0-20% 2M NH3 in MeOH/DCM

Sources & evidence

ORD record
ord-71b9897385b34b5bb32f9468d007c604
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883819B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes