1,1'-Carbonyldiimidazole → HCID 49771648, compound

HRID 639605Notes

Reaction equation

HRID 639605 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.C([N:20](CC1C=CC=CC=1)[C:21]1[C:26]([NH2:27])=[C:25]([NH:28][CH2:29][C:30]2[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=2)[CH:24]=[C:23]([C:37]2[O:38][CH:39]=[CH:40][N:41]=2)[N:22]=1)C1C=CC=CC=1>C1COCC1>[NH2:20][C:21]1[C:26]2[NH:27][C:6](=[O:7])[N:28]([CH2:29][C:30]3[CH:31]=[N:32][C:33]([CH3:36])=[CH:34][CH:35]=3)[C:25]=2[CH:24]=[C:23]([C:37]2[O:38][CH:39]=[CH:40][N:41]=2)[N:22]=1

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 67454526HCID 67454526, compound

Product 1

HCID 49771648HCID 49771648, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

CDI (272 mg) was added to a solution of N2,N2-dibenzyl-N4-(6-methyl-pyridin-3-ylmethyl)-6-oxazol-2-yl-pyridine-2,3,4-triamine (400 mg) in THF (10 ml). The solution was left to stir under N2 at 60° C. for 5 h. A further 3 equivalents of CDI (408 mg) were added and the reaction heated at reflux for 16 h. The reaction mixture was allowed to cool then concentrated in vacuo. The crude mixture was then dissolved in concentrated H2SO4 (5 ml) and left for 30 minutes at RT. The dark brown solution was added drop-wise onto crushed ice. The pH was adjusted to ˜8 by addition of a saturated solution of K2CO3 then the mixture was filtered. The solid obtained was washed with EtOAc (50 ml) then the organic and aqueous filtrates were transferred to a separating funnel. The layers were separated and the aqueous was re-extracted with EtOAc (50 ml). The organics were combined, dried (MgSO4) and evaporated to provide a gummy solid. This was triturated with Et2O and the solid collected by filtration and washed with Et2O, giving the title compound as an off-white solid (30 mg). 1H NMR (CDCl3, 400 MHz) □ 2.45 (s, 3H), 5.09 (s, 2H), 7.21-7.28 (m, 2H), 7.30 (s, 1H), 7.70 (dd, 1H), 7.95 (s, 1H), 8.42 (d, 1H). LCMS rt=2.29 m/z 323 [MH]+

Workup

  1. waitThe solution was left
  2. temperaturethe reaction heated
  3. temperatureat reflux for 16 h
  4. temperatureto cool
  5. concentrationthen concentrated in vacuo
  6. dissolutionThe crude mixture was then dissolved in concentrated H2SO4 (5 ml)
  7. waitleft for 30 minutes at RT
  8. additionThe dark brown solution was added drop-wise
  9. customonto crushed ice
  10. additionThe pH was adjusted to ˜8 by addition of a saturated solution of K2CO3
  11. filtrationthe mixture was filtered
  12. customThe solid obtained
  13. washwas washed with EtOAc (50 ml)
  14. customthe organic and aqueous filtrates were transferred to a separating funnel
  15. customThe layers were separated
  16. extractionthe aqueous was re-extracted with EtOAc (50 ml)
  17. dry with materialdried (MgSO4)
  18. customevaporated
  19. customto provide a gummy solid
  20. customThis was triturated with Et2O
  21. filtrationthe solid collected by filtration
  22. washwashed with Et2O

Sources & evidence

ORD record
ord-060ffdc530ab4f6dba66e1a531c994c2
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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