Hydrochloric Acid → 3-({5-[(4-Fluorophenyl)carbamoyl]pyrimidin-2-yl}sulfanyl)benzoic acid

HRID 348437Notes

Reaction equation

HRID 348437 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].CC(C)([O-])C.[K+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:28]=[N:29][C:30](S(C)=O)=[N:31][CH:32]=2)=[O:26])=[CH:20][CH:19]=1.Cl>C1COCC1.CO.ClCCl.O>[F:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25]([C:27]2[CH:32]=[N:31][C:30]([S:1][C:2]3[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=3)[C:5]([OH:7])=[O:6])=[N:29][CH:28]=2)=[O:26])=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 95737Benzoic acid, 3-mercapto-HCID 23665647Potassium tert-butoxideHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 160047993-({5-[(4-Fluorophenyl)carbamoyl]pyrimidin-2-yl}sulfanyl)benzoic acidYield 23%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent2×

Procedure

To a solution of 3-mercaptobenzoic acid (83 mg, 0.54 mmol) in THF (2.5 mL) was added potassium tert-butoxide (1 M in THF, 1.1 ML, 1.1 mmol). After 3 min, 2-methane-sulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide was added in one portion and the solution was stirred for 24 h. Water was added, and then the solution was poured into 3% HCl to precipitate the product. The solids were collected by filtration and washed with water. Flash chromatography on SiO2 using a gradient of 5% methanol/dichloromethane to 10% methanol/dichloromethane afforded 15.1 mg (23% yield) of the titled thioether as a white solid. API-MS m/z 370 (MH+), 368 (M−H)−.

Workup

  1. customto precipitate the product
  2. filtrationThe solids were collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-730b08d4143242b1856fde3ac9f5e433
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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