Potassium Carbonate → HCID 59485709, compound

HRID 1972207Notes

Reaction equation

HRID 1972207 reaction equation
[OH: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]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:11][O:10][C:9]2=[O:23])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH4+:30].[Cl-:31]>CN(C=O)C>[Cl:31][C:5]1[N:8]=[N:30][C:2]([O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C@@H:12]([C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=4)[CH2:11][O:10][C:9]3=[O:23])=[CH:6][CH:7]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 59485749HCID 59485749, compound

Product 1

HCID 59485709HCID 59485709, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (S)-3-(4-hydroxy-phenyl)-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one (20 mg, 0.062 mmol), 3,6-dichloropyradazine (18.5 mg, 0.124 mmol) and K2CO3 (17 mg, 0.124 mmol) in DMF (0.5 mL) is heated to 80° C. for 2 h and then cooled down to room temperature. The mixture is then treated with saturated NH4Cl aqueous solution (4 mL) and extracted with EtOAc (3×2 mL). The combined organic layers were then concentrated and purified by preparative LC/MS to provide the desired product (S)-3-[4-(6-Chloro-pyridazin-3-yloxy)-phenyl]-4-(3-trifluoromethyl-phenyl)-oxazolidin-2-one. 1H NMR (CDCl3, 400 MHz) δ 7.50˜7.63 (m, 4H), 7.47 (d, 1H), 7.42 (d, 2H), 7.09˜7.15 (m, 3H), 5.46 (dd, 1H), 4.82 (t, 1H), 4.19 (dd, 1H); HPLC-MS calculated for C20H13ClF3N3O3 (M+H+) 436.1, found 436.1.

Workup

  1. temperaturecooled down to room temperature
  2. extractionextracted with EtOAc (3×2 mL)
  3. concentrationThe combined organic layers were then concentrated
  4. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-ebf8116e501b460f8f4eaa2ee4995318
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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