1,4-Dioxane hydrochloride → HCID 118023049, compound

HRID 1498866Notes

Reaction equation

HRID 1498866 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][C:15]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[N:16][CH:17]=2)([CH3:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.Cl.O1CCOCC1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]([C:12]2[CH:13]=[N:14][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[N:16][CH:17]=2)([CH3:11])[CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 118023536HCID 118023536, compound

Product 1

HCID 118023049HCID 118023049, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 4-(5-(2-(4-fluorophenyl)-1-hydroxypropan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate (450 mg, 1.08 mmol) in DCM (20 mL) was added 4 M HCl/1,4-dioxane (3 mL). After stirred at RT for 15 h, the reaction mixture was concentrated, the residue was diluted by aq. NaHCO3 (20 mL) and extracted with DCM. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was separated by chiral Prep-HPLC to give (R)-2-(4-fluorophenyl)-2-(2-(piperazin-1-yl)pyrimidin-5-yl)propan-1-ol (100 mg, 29%) as a white solid. MS (ES+) C17H21FN4O requires: 316. found: 317 [M+H]+. Chiral HPLC, Column: IC 4.6*150 mm 5 um, Co-Solvent: EtOH:Hexane=1:1 (0.1% DEA), RT=4.22 min.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue was diluted by aq. NaHCO3 (20 mL)
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was separated by chiral Prep-HPLC

Sources & evidence

ORD record
ord-de822071537345c6a075fc68c2f9b568
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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