Cesium carbonate → HCID 58042761, compound

HRID 564179Notes

Reaction equation

HRID 564179 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:20]=[CH:19][C:7]2[CH2:8][CH2:9][N:10](C(=O)C(F)(F)F)[CH2:11][CH2:12][C:6]=2[CH:5]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:27][C:28]1[CH:42]=[CH:41][C:31]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][NH:37][C:36](=[O:40])[CH:35]=2)=[CH:30][CH:29]=1.[OH-].[Na+]>CN(C=O)C>[F:27][C:28]1[CH:42]=[CH:41][C:31]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][N:37]([CH2:2][CH2:3][C:4]3[CH:20]=[CH:19][C:7]4[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=4[CH:5]=3)[C:36](=[O:40])[CH:35]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 86623683HCID 86623683, compound

Product 1

HCID 58042761HCID 58042761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.05 g (3.42 mmol) 1-[7-(2-chloro-ethyl)-1,2,4,5-tetrahydro-3-benzazepin-3-yl]-2,2,2-trifluoro-ethanone in 5 mL DMF is added at 0° C. cesium carbonate and after 15 min 600 mg (2.74 mmol) 4-(4-fluoro-benzyloxy)-1H-pyridin-2-one (preparation 22.1). The reaction mixture is stirred overnight at RT and is then added to 50 mL 1 M aqueous NaOH-solution. The mixture is stirred 2 h at RT. The aqueous phase is extracted with tert-butylmethylether. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile (0.15% formic acid) 95:5 to 5:95).

Workup

  1. stirringThe mixture is stirred 2 h at RT
  2. extractionThe aqueous phase is extracted with tert-butylmethylether
  3. dry with materialThe combined organic phase is dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.15% formic acid)/acetonitrile (0.15% formic acid) 95:5 to 5:95)

Sources & evidence

ORD record
ord-75f5d1499e4a42289deb6e5da3b5629e
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

Loading…