Triazabicyclodecene → HCID 86695684, compound

HRID 335324

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]

Participants

6

Reactant 3

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

Product 1

HCID 86695684HCID 86695684, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

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
Patent number
US08883819B2

Linked notes

Loading…