Cesium carbonate → HCID 71201938, compound

HRID 1908681Notes

Reaction equation

HRID 1908681 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C@H:13]2[CH2:15][C@@H:14]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.[O:22]1[CH2:25][CH:24]([OH:26])[CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[O:22]1[CH2:25][CH:24]([O:26][C:2]2[N:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C@H:13]3[CH2:15][C@@H:14]3[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:12])[CH3:9])=[CH:4][CH:3]=2)[CH2:23]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 9942117Oxetan-3-olHCID 71487163HCID 71487163, compound2×

Product 1

HCID 71201938HCID 71201938, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

(1S,2S)-2-Phenyl-cyclopropanecarboxylic acid [(S)-1-(6-chloro-pyridin-3-yl)-ethyl]-amide (Compound 18) (2.00 g, 6.65 mmol) was dissolved in DMF (50 ml). Oxetan-3-ol (4.00 g, 54 mmol) and dicesium carbonate (16.2 g, 49.9 mmol) were added and the mixture was heated at 100° C. ON. The mixture was poured out into brine and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and was filtered and then evaporated to dryness. The residue was transferred to a silica gel column and eluded with EtOAc/heptanes 1:1 to give Compound 19 as a solid. This solid was dissolved in a mixture of THF (10 ml), EtOAc (20 mL) and heptanes (10 ml). The mixture was concentrated to approx. 15 mL in vacuo and this solution was cooled in an ice/water bath. A white precipitate formed. The solids was collected by filtration and dried in vacuo to give the title compound as colorless crystals (0.097 g, 4%). %). 1H-NMR (500 MHz, DMSO) δ 8.55 (d, 1H), 8.04 (s, 1H), 7.70 (d, 1H), 7.25 (m, 2H), 7.15 (m, 1H), 7.10 (d, 2H), 6.87 (d, 1H), 5.52 (m, 1H), 4.95 (m, 1H), 4.87 (m, 2H), 4.53 (m, 2H), 2.20 (m, 1H), 1.90 (m, 1H), 1.37 (m, 4H), 1.21 (m, 1H). LC-MS (m/z) 339.2 (MH+), tR=0.63 min (method B). Mp=151-153 C.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationwas filtered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b7c3e7ae036045c8ae8d3753d329e8f9
Source dataset
uspto-grants-2013_12
Patent number
US08598213B2

Reaction notes

Loading…