Cyclopropanecarboxylic acid → HCID 89691182, compound

HRID 2202859Notes

Reaction equation

HRID 2202859 reaction equation
CN(C(ON1N=N[C:11]2C=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:25][C:26]1[CH:27]=[C:28]([NH:33][CH2:34][CH3:35])[C:29]([NH2:32])=[CH:30][CH:31]=1.[CH:36](N(CC)C(C)C)(C)[CH3:37].C1(C(O)=O)CC1>CN(C=O)C>[Br:25][C:26]1[CH:31]=[CH:30][C:29]2[N:32]=[C:34]([CH:35]3[CH2:11][CH2:10]3)[N:33]([CH2:36][CH3:37])[C:28]=2[CH:27]=1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 592936595-broMo-N1-ethylbenzene-1,2-diaMine

Product 1

HCID 89691182HCID 89691182, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (4.89 g) was added to a solution of 4-bromo-N2-ethylbenzene-1,2-diamine (2.63 g), N,N-diisopropylethylamine (6.40 ml) and cyclopropanecarboxylic acid (0.979 ml) in DMF (40 ml) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was dissolved into AcOH (40.0 ml), and the mixture was stirred at 80° C. for 1 h. After concentration of the mixture, the residue was neutralized with saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (1.2 g) as a pale yellow solid.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved into AcOH (40.0 ml)
  8. stirringthe mixture was stirred at 80° C. for 1 h
  9. extractionextracted with EtOAc
  10. customThe organic layer was separated
  11. washwashed with water and brine
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-5b9498cb6ba3470ea56cb73539800dc1
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…