Dimethyl Sulfoxide → HCID 89690092, compound

HRID 517931Notes

Reaction equation

HRID 517931 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]1[C:21]2[C:16](=[N:17][C:18]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)[N:20]=2)[N:15]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]=[C:12]1[C:21]2[C:16](=[N:17][C:18]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)=[C:19]([C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)[N:20]=2)[N:15]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 89689927HCID 89689927, compound

Product 1

HCID 89690092HCID 89690092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of oxalyl chloride (0.085 ml, 0.973 mmol) in DCM (20 ml) at −78° C. under nitrogen was added a dropwise solution of DMSO (0.168 ml, 2.373 mmol) in DCM (10 ml). After stirring at −78° C. for two hours, a solution of tert-butyl 8-hydroxy-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 1) (200 mg, 0.463 mmol) in DCM (5 ml) was added dropwise and the mixture was left to stir for 15 minutes at −78° C. under an atmosphere of nitrogen. Triethylamine (0.331 ml, 2.373 mmol) was added and after 5 minutes the reaction mixture allowed to warm to 18° C. under an atmosphere of nitrogen overnight. The reaction mixture was diluted with DCM (30 ml) and was sequentially washed with 2M NaOH (30 ml), water (30 ml) and brine (30 ml). The organic layer was separated and dried using a hydrophobic frit and the solvent evaporated to afford the titled compound as a yellow solid;

Workup

  1. waitthe mixture was left
  2. stirringto stir for 15 minutes at −78° C. under an atmosphere of nitrogen
  3. temperatureto warm to 18° C. under an atmosphere of nitrogen overnight
  4. washwas sequentially washed with 2M NaOH (30 ml), water (30 ml) and brine (30 ml)
  5. customThe organic layer was separated
  6. customdried
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-e1e1187058e1477d860c1b7e51118e4b
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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