Cesium carbonate → HCID 58635338, compound

HRID 1351612Notes

Reaction equation

HRID 1351612 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][NH2:19])[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:21]1[N:26]=[CH:25][C:24]([CH2:27][CH3:28])=[CH:23][N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:27]([C:24]1[CH:23]=[N:22][C:21]([NH:19][CH2:18][CH:15]2[CH2:14][CH2:13][N:12]([C:10]([C@@H:8]3[CH2:9][C@H:7]3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:11])[CH2:17][CH2:16]2)=[N:26][CH:25]=1)[CH3:28]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 35727632-Chloro-5-ethylpyrimidineHCID 58635332HCID 58635332, compound

Product 1

HCID 58635338HCID 58635338, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

The stirred reaction mixture of (1-{[(1R,2R)-2-phenylcyclopropyl]carbonyl}piperidin-4-yl)methylamine (EXAMPLE 154, STEP 2) (0.100 g, 0.387 mmol), 2-chloro-5-ethyl-pyrimidine ([111196-81-7], 0.055 g, 0.387 mmol) and cesium carbonate (0.252 g, 0.774 mmol) in DMF (5 mL) was heated at 150° C. for 7 h. The reaction mixture was cooled to RT, diluted with ethyl acetate (100 mL), washed with water (5×20 mL), and brine (10 mL), then dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel 60, eluting with 10:1-20:89-70 CH2Cl2:2-propanol:hexane to give the title compound. M.S. (M+1): 365.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. washwashed with water (5×20 mL), and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel 60
  7. washeluting with 10:1-20:89-70 CH2Cl2

Sources & evidence

ORD record
ord-a17c0574d0174445b588d82dc2a8de39
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

Loading…