1,4-Dioxane → HCID 89689897, compound

HRID 517933Notes

Reaction equation

HRID 517933 reaction equation
[OH:1][C:2]1([CH3:33])[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:10]=2)[N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.O1CCOCC1>Cl>[CH3:33][C:2]1([OH:1])[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[N:10]=2)[NH:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 89689976HCID 89689976, compound

Product 1

HCID 89689897HCID 89689897, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl 8-hydroxy-8-methyl-2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (step 3) (310 mg, 0.696 mmol) in 4M HCl in dioxane (2 ml, 8.00 mmol) was stirred at room temperature for 30 mins. The reaction mixture was concentrated under reduced pressure and the residue partitioned between saturated aqueous sodium bicarbonate and DCM. The organic portion was separated and the aqueous portion extracted with DCM (30 ml). The combined organic layers concentrated under reduced pressure to afford the titled compound;

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between saturated aqueous sodium bicarbonate and DCM
  3. customThe organic portion was separated
  4. extractionthe aqueous portion extracted with DCM (30 ml)
  5. concentrationThe combined organic layers concentrated under reduced pressure

Sources & evidence

ORD record
ord-73decd8da27d4fbd95802256704074be
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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