1,1'-Carbonyldiimidazole → HCID 178505196, compound

HRID 1890357Notes

Reaction equation

HRID 1890357 reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([NH:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[N:7]=1)(=[O:4])=[O:3].C1N=CN([C:25](N2C=NC=C2)=[O:26])C=1>C1COCC1>[CH3:1][S:2]([O:5][C:6]1[N:7]=[C:8]2[N:13]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[C:25]([OH:26])=[N:12][C:9]2=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 866552605-Amino-6-(cyclohexylamino)pyridin-2-yl Methanesulfonate

Product 1

HCID 178505196HCID 178505196, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

5-Amino-6-(cyclohexylamino)pyridin-2-yl methanesulfonate (1.44 g, 5.05 mmol) was dissolved in THF (30 mL) and CDI (2.455 g, 15.14 mmol) was added. The mixture was heated at 70° C. for 3 h. THF was removed and the residue was dissolved in EtOAc. The resulting solution was washed with water followed by 1 M HCl, dried over MgSO4 and concentrated under reduced pressure to give the title compound (0.96 g) without further purification. LCMS m/z=312.50 [M+H]+.

Workup

  1. customTHF was removed
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe resulting solution was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d8bd6f6e32274b07b4ba1a291671ebb3
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

Loading…