Potassium Carbonate → HCID 66652757, compound

HRID 2283613Notes

Reaction equation

HRID 2283613 reaction equation
[C:1]([O:5][C:6](=[O:25])[N:7]([S:13]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19](F)=[CH:18][C:17]=1[F:24])(=[O:15])=[O:14])[C:8]1[N:9]=[CH:10][S:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:26][C:27]1[CH:32]=[C:31]([C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[OH:40])[CH:30]=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O.O>[C:1]([O:5][C:6](=[O:25])[N:7]([S:13]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([O:40][C:34]2[CH:35]=[CH:36][C:37]([F:39])=[CH:38][C:33]=2[C:31]2[CH:30]=[CH:29][N:28]=[C:27]([NH2:26])[CH:32]=2)=[CH:18][C:17]=1[F:24])(=[O:14])=[O:15])[C:8]1[N:9]=[CH:10][S:11][CH:12]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 59436581Tert-butyl (5-chloro-2,4-difluorophenyl)sulfonyl(thiazol-4-yl)carbamateHCID 136365471HCID 136365471, compound

Product 1

HCID 66652757HCID 66652757, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

tert-Butyl[(5-chloro-2,4-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 4, 60 mg, 0.15 mmol) was added to a mixture of 2-(2-aminopyridin-4-yl)-4-fluorophenol (Preparation 21, 30 mg, 0.1 mmol) and potassium carbonate (41 mg, 0.29 mmol) in dimethylsulfoxide (2 mL) and stirred at ambient temperature for 24 hours. The reaction mixture was poured into saturated aqueous ammonium chloride and water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was taken up in dichloromethane, concentrated onto diatomaceous earth, and purified by automated silica gel flash chromatography (100% hexanes to 20% methanol in ethyl acetate, gradient elution) to afford tert-butyl({4-[2-(2-aminopyridin-4-yl)-4-fluorophenoxy]-5-chloro-2-fluorophenyl}sulfonyl)1,3-thiazol-4-ylcarbamate as a light brown oil, which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationconcentrated onto diatomaceous earth
  7. custompurified by automated silica gel flash chromatography (100% hexanes to 20% methanol in ethyl acetate, gradient elution)

Sources & evidence

ORD record
ord-a4565904f58749738444a21bc2c0f185
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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