Hydrochloric Acid → HCID 71244917, compound

HRID 1774614Notes

Reaction equation

HRID 1774614 reaction equation
Cl.[CH3:2][O:3][C:4]([CH:6]1[CH2:11][N:10]([C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[N:15]=[CH:14][N:13]=2)[CH2:9][CH2:8][N:7]1C(OC(C)(C)C)=O)=[O:5]>O1CCOCC1>[CH3:2][O:3][C:4]([CH:6]1[CH2:11][N:10]([C:12]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=3)[N:15]=[CH:14][N:13]=2)[CH2:9][CH2:8][NH:7]1)=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71240780HCID 71240780, compound

Product 1

HCID 71244917HCID 71244917, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M HCl in dioxane solution (8 ml) was added in one portion to a stirred solution of 4-[6-(3,4-Dichloro-phenyl)-pyrimidin-4-yl]-piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.36 g, 0.75 mmol) in dioxane (2 ml) and the mixture was stirred at room temperature overnight. After this time the reaction mixture was concentrated and the resulting residue was partitioned between DCM (100 ml) and saturated sodium bicarbonate (75 ml) and stirred at room temperature for 10 minutes. The mixture was then extracted with DCM (3×100 ml), the organic layers were combined, separated and washed with brine (50 ml). The organic layer was removed, dried (MgSO4) filtered and concentrated to give the title compound (0.27 g, 87% yield) as a yellow solid.

Workup

  1. concentrationAfter this time the reaction mixture was concentrated
  2. customthe resulting residue was partitioned between DCM (100 ml) and saturated sodium bicarbonate (75 ml)
  3. stirringstirred at room temperature for 10 minutes
  4. extractionThe mixture was then extracted with DCM (3×100 ml)
  5. customseparated
  6. washwashed with brine (50 ml)
  7. customThe organic layer was removed
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-b9ba49df27e542ae9477436c7a321bb6
Source dataset
uspto-grants-2016_02
Patent number
US09260422B2

Reaction notes

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