Water → HCID 59486076, compound

HRID 1972295Notes

Reaction equation

HRID 1972295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH2:11][NH:10][C:9]2=[O:20])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].O.C[N:29]([CH:31]=O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:5]4[N:8]=[N:29][CH:31]=[CH:3][CH:4]=4)[CH:14]=3)[CH2:11][NH:10][C:9]2=[O:20])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 68707133HCID 68707133, compound

Product 1

HCID 59486076HCID 59486076, compound

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-1-(4-chlorophenyl)-5-(3-hydroxyphenyl)imidazolidin-2-one (210 mg, 0.73 mmol, prepared by using a similar procedure as described in Example 460) and 3-chloropyradazine (167 mg, 1.46 mmol) in DMF (2 mL) is added Cs2CO3 (354 mg, 1.09 mmol). The mixture is stirred at 80° C. for 14 h and is then cooled to room temperature. The reaction mixture is then treated with water (20 mL) and extracted with EtOAc (3×15 ml). The combined organic layers are washed with brine and dried (MgSO4). After removing the drying agent, the solution is concentrated and purified by flash column chromatography (silica gel, 0%˜10% MeOH/CH2Cl2) to provide the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.95 (dd, J=4.4, 1.2 Hz, 1H), 7.49 (dd, J=8.8, 4.4 Hz, 1H), 7.32-7.40 (m, 3H), 7.10-7.20 (m, 6H), 5.28 (dd, J=8.0, 4.8 Hz, 1H), 4.70 (br s, 1H), 3.97 (t, J=8.8 Hz, 1H), 3.41 (dd, J=8.8, 6.0 Hz, 1H); HPLC-MS calculated for C19H15ClN4O2 (M+H+) 367.1, found 367.1.

Workup

  1. temperatureis then cooled to room temperature
  2. extractionextracted with EtOAc (3×15 ml)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried (MgSO4)
  5. customAfter removing the drying agent
  6. concentrationthe solution is concentrated
  7. custompurified by flash column chromatography (silica gel, 0%˜10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7bda3c5bcd9d4fe888f7b8c221fab3e4
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

Loading…