Pyridine → HCID 86692829, compound

HRID 518771Notes

Reaction equation

HRID 518771 reaction equation
[OH:1][CH:2]1[CH2:5][C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)([C:6]#[N:7])[CH2:3]1.N1C=CC=CC=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[CH3:20][S:21]([O:1][CH:2]1[CH2:5][C:4]([C:6]#[N:7])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:3]1)(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 59471552HCID 59471552, compound

Product 1

HCID 86692829HCID 86692829, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxy-1-(pyridin-2-yl)cyclobutanecarbonitrile (WO 2007/060484)(10.996 g, 63.1 mmol) in dry DCM (100 mL) and pyridine (20.59 mL, 252 mmol), was added (with stirring and cooling in an ice water bath) methane sulfonyl chloride (4.88 mL, 63.1 mmol). The mixture was stirred at RT for 25 hours. The solvent was removed at reduced pressure, and the residue was partitioned between EtOAc and aqueous NaHCO3. The organic phase was washed with aqueous NaHCO3 and was concentrated at reduced pressure. The residue was eluted through a short pad of silica gel (eluent 30%-50% EtOAc/hexane). The solvent was removed, and the resulting oil was crystallized from toluene on dilution with hexane to afford the title compound as a 3:1 mixture of geometrical isomers (assessed by NMR).

Workup

  1. customThe solvent was removed at reduced pressure
  2. customthe residue was partitioned between EtOAc and aqueous NaHCO3
  3. washThe organic phase was washed with aqueous NaHCO3
  4. concentrationwas concentrated at reduced pressure
  5. washThe residue was eluted through a short pad of silica gel (eluent 30%-50% EtOAc/hexane)
  6. customThe solvent was removed
  7. customthe resulting oil was crystallized from toluene on dilution with hexane

Sources & evidence

ORD record
ord-43422dc0c5a241b99d280081ac93d397
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…