Cesium carbonate → HCID 16068007, compound

HRID 887980Notes

Reaction equation

HRID 887980 reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[NH:7]/[C:6](=[CH:11]\[C:12]2[N:13]=[CH:14][O:15][C:16]=2[C:17]([CH3:20])([CH3:19])[CH3:18])/[C:5]1=[O:21])(=O)C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:17]([C:16]1[O:15][CH:14]=[N:13][C:12]=1/[CH:11]=[C:6]1/[C:5](=[O:21])[NH:4]/[C:9](=[CH:27]\[C:26]2[CH:29]=[CH:30][CH:31]=[C:24]([O:23][CH3:22])[CH:25]=2)/[C:8](=[O:10])[NH:7]/1)([CH3:18])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115693-MethoxybenzaldehydeHCID 58852012HCID 58852012, compound

Product 1

HCID 16068007HCID 16068007, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4 (50 mg, 0.17 mmol) in DMF (4 mL) was added 3-methoxybenzaldehyde (31.4 μL, 0.26 mmol) and the solution was repeatedly evacuated in a short time to remove oxygen and flushed with Ar, followed by the addition of Cs2CO3 (111.9 mg, 0.34 mmol) and the evacuation-flushing process was repeated again. The resultant mixture was heated for 3 h at 85□. After the solvent was removed by evaporation, the residue was AcOEt, washed with water for two times and saturated NaCl for three times, dried over Na2SO4 and concentrated in vacuo. The resulting residue was dissolved in 70% MeCN aq and applied to reverse-phase HPLC column (μBondasphere 5C18 100 A, 19×150 mm) and eluted using a linear gradient from 30 to 100% CH3CN in 0.1% TFA aq over 30 min at a flow rate of 12 mL/min, and the desired fraction was collected and concentrated by evaporation to give a 35.3 mg (55.9%) of yellow colored KPU-201. mp 114-116° C.; 1H NMR (300 MHz, CDCl3) δ 11.40 (br s, 1H), 8.14 (br s, 1H), 7.88 (s, 1H), 6.96-7.00 (m, 2H), 6.92 (s, 1H), 6.88 (s, 1H), 6.88-6.92 (m, 1H), 3.83 (s, 3H), 1.44 (s, 9H); HRMS (EI) m/z 367.1538 (M+) (calcd for C20H21N3O4: 367.1532).

Workup

  1. customthe solution was repeatedly evacuated in a short time
  2. customto remove oxygen
  3. customflushed with Ar
  4. customAfter the solvent was removed by evaporation
  5. washwashed with water for two times and saturated NaCl for three times
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe resulting residue was dissolved in 70% MeCN aq
  9. washeluted
  10. customover 30 min
  11. customthe desired fraction was collected
  12. concentrationconcentrated by evaporation
  13. customto give a 35.3 mg (55.9%) of yellow colored KPU-201

Sources & evidence

ORD record
ord-f3cdb08640e74a1cbdbbf3c25e264ebd
Source dataset
uspto-grants-2012_08
Patent number
US08247552B2

Reaction notes

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