Potassium Carbonate → HCID 86682364, compound

HRID 2283637Notes

Reaction equation

HRID 2283637 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[OH:18])[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[C:27](F)=[CH:28][C:29]([F:54])=[C:30]([S:32]([N:35]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=2[O:52][CH3:53])[C:36]2[N:41]=[CH:40][C:39]([F:42])=[CH:38][N:37]=2)(=[O:34])=[O:33])[CH:31]=1>CS(C)=O.O>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:17])[F:16])[CH:11]=[CH:10][C:9]=2[O:18][C:27]2[C:26]([Cl:25])=[CH:31][C:30]([S:32]([N:35]([CH2:43][C:44]3[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][C:45]=3[O:52][CH3:53])[C:36]3[N:37]=[CH:38][C:39]([F:42])=[CH:40][N:41]=3)(=[O:33])=[O:34])=[C:29]([F:54])[CH:28]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66653220HCID 66653220, compoundHCID 136387753HCID 136387753, compound

Product 1

HCID 86682364HCID 86682364, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2-(2-Aminopyridin-4-yl)-4-(trifluoromethyl)phenol (Preparation 17, 0.93 g, 3.6 mmol) was taken up in dimethylsulfoxide (40 mL) and potassium carbonate (0.95 g, 6.9 mmol) was added followed by 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(5-fluoropyrimidin-2-yl)benzenesulfonamide (Preparation 19, 1.73 g, 3.64 mmol). The reaction mixture was stirred for 18 hours then diluted with water (120 mL) and the solid collected by filtration. The filtrate was extracted with ethyl ether. The solid was dissolved in dichloromethane and combined with the ether extract. The combined organic solution was dried over anhydrous magnesium sulfate, treated with activated carbon and filtered through a pad of diatomaceous earth. The solvent was concentrated in vacuo to give a thick oil. The oil was purified by silica gel column chromatography (0 to 5% methanol in dichloromethane gradient elution) and concentrated in vacuo to afford the title compound as a glass (2.24 g).

Workup

  1. filtrationthe solid collected by filtration
  2. extractionThe filtrate was extracted with ethyl ether
  3. dissolutionThe solid was dissolved in dichloromethane
  4. extractionextract
  5. dry with materialThe combined organic solution was dried over anhydrous magnesium sulfate
  6. additiontreated with activated carbon
  7. filtrationfiltered through a pad of diatomaceous earth
  8. concentrationThe solvent was concentrated in vacuo
  9. customto give a thick oil
  10. customThe oil was purified by silica gel column chromatography (0 to 5% methanol in dichloromethane gradient elution)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0857fc3a0fa34ff7af0fb4cfdb57ce08
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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