Potassium Carbonate → HCID 56598617, compound

HRID 2283605Notes

Reaction equation

HRID 2283605 reaction equation
[F:1][C:2]1[C:3]([C:15]([F:18])([F:17])[F:16])=[CH:4][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[N:11][CH:10]=2)=[C:6]([OH:8])[CH:7]=1.C(OC(=O)[N:25]([S:31]([C:34]1[CH:39]=[C:38]([Cl:40])[C:37](F)=[CH:36][C:35]=1[F:42])(=[O:33])=[O:32])[C:26]1[N:27]=[CH:28][S:29][CH:30]=1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O.O>[Cl:40][C:38]1[C:37]([O:8][C:6]2[CH:7]=[C:2]([F:1])[C:3]([C:15]([F:16])([F:18])[F:17])=[CH:4][C:5]=2[C:9]2[CH:14]=[CH:13][N:12]=[N:11][CH:10]=2)=[CH:36][C:35]([F:42])=[C:34]([S:31]([NH:25][C:26]2[N:27]=[CH:28][S:29][CH:30]=2)(=[O:32])=[O:33])[CH:39]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 59436581Tert-butyl (5-chloro-2,4-difluorophenyl)sulfonyl(thiazol-4-yl)carbamateHCID 1360636295-Fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenol

Product 1

HCID 56598617HCID 56598617, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-fluoro-2-pyridazin-4-yl-4-(trifluoromethyl)phenol (Preparation 9, 2.81 g, 10.9 mmol), tert-butyl[(5-chloro-2,4-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 4, 5.59 g, 13.6 mmol) and potassium carbonate (4.51 g, 32.6 mmol) in dimethylsulfoxide (20 mL) was heated at 75° C. for 24 hours. The reaction mixture was cooled to ambient temperature, diluted with water, neutralized with saturated aqueous ammonium chloride, then extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via automated silica gel flash chromatography using two runs, (10% to 100% ethyl acetate in hexanes gradient elution for run 1, and 0% to 10% methanol in dichloromethane gradient elution for run 2) to afford the title compound as a brown solid. (2.42 g, 41%)

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washtwo runs, (10% to 100% ethyl acetate in hexanes gradient elution for run 1, and 0% to 10% methanol in dichloromethane gradient elution for run 2)

Sources & evidence

ORD record
ord-2a150b6697554a24b9a452f44b0d73d5
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

Loading…