1,1'-Thiocarbonyldiimidazole → HCID 89690173, compound

HRID 517903Notes

Reaction equation

HRID 517903 reaction equation
[OH:1][CH:2]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=[C:4]2[CH:3]1[OH:33].[C:34](N1C=CN=C1)(N1C=CN=C1)=[S:35]>O1CCCC1>[S:35]=[C:34]1[O:33][CH:3]2[C:4]3[C:5]([N:24]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[CH2:25][CH:2]2[O:1]1)=[N:6][C:7]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)=[C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[N:9]=3

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 66665909rac-Tert-butyl 7,8-dihydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Product 1

HCID 89690173HCID 89690173, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 7,8-di hydroxy-2,3-d i-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 2) (1.28 g, 2.86 mmol) was dissolved in tetrahydrofuran (50 ml). 1,1′-Thiocarbonyl diimidazole (1.019 g, 5.72 mmol) was added and the solution heated at reflux for 3 h. The reaction mixture was cooled to room temperature and evaporated to dryness. Water and DCM (300 ml) were added. The organic layer was separated and evaporated to dryness. Ethyl acetate (5 ml) was added to the dark residue and the resulting solid filtered off. The solid was washed twice with EtOAc (5 ml) to afford the titled compound;

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 3 h
  3. customevaporated to dryness
  4. additionWater and DCM (300 ml) were added
  5. customThe organic layer was separated
  6. customevaporated to dryness
  7. additionEthyl acetate (5 ml) was added to the dark residue
  8. filtrationthe resulting solid filtered off
  9. washThe solid was washed twice with EtOAc (5 ml)

Sources & evidence

ORD record
ord-8238023a7acf4b1f9fb972d1f5faa036
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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