Pyridine → Methyl [2-(4,6-dimethoxypyrimidin-2-yloxy)-6-fluorophenylsulfamoyl]acetate

HRID 1418821Notes

Reaction equation

HRID 1418821 reaction equation
Cl[S:2]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])=[O:3].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([O:20][C:21]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:22]=2[NH2:23])[N:13]=1.N1C=CC=CC=1>ClCCl>[CH3:19][O:18][C:16]1[CH:17]=[C:12]([O:11][CH3:10])[N:13]=[C:14]([O:20][C:21]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:22]=2[NH:23][S:2]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])=[O:3])[N:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11435213Methyl (chlorosulfonyl)acetateHCID 543689482-(4,6-Dimethoxypyrimidin-2-yloxy)-6-fluoroaniline

Product 1

HCID 54135497Methyl [2-(4,6-dimethoxypyrimidin-2-yloxy)-6-fluorophenylsulfamoyl]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl (chlorosulfonyl)acetate (13.0 g) in dichloromethane (20 ml) was aaded dropwise with stirring and cooling to 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-fluoroaniline (20 g) and pyridine (6.3 g) in dichloromethane (120 ml). After stirring for 2 hours, the mixture was allowed to stand at room temperature overnight. Washing with dilute hydrochloric acid and water, dryiny over magnesium sulfate, and running down, gave an oil which was triturated with ether. The resulting off-white solid was separated by filtration to qive 20.4 of the desired product, mp 111°-114° C.

Workup

  1. stirringAfter stirring for 2 hours
  2. washWashing with dilute hydrochloric acid and water
  3. customgave an oil which
  4. customwas triturated with ether
  5. customThe resulting off-white solid was separated by filtration

Sources & evidence

ORD record
ord-a1c1dc7004cb4a7e979a0f6c20457708
Source dataset
uspto-grants-1999_03
Patent number
US05885935

Reaction notes

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