Potassium Carbonate → HCID 90022747, compound

HRID 1772985Notes

Reaction equation

HRID 1772985 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)(=[O:10])=[O:9].[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25][NH2:26].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:24]=1[CH2:25][NH:26][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 848332-Chloro-6-fluorobenzylamineHCID 516892Sodium BicarbonateHCID 64280908HCID 64280908, compound

Product 1

HCID 90022747HCID 90022747, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-Chloro-N-(3,4-dimethoxyphenyl)pyridine-3-sulfonamide (IntD1) (0.5 g, 1.50 mmol), 2-chloro-6-fluoro-benzylamine (0.26 g, 1.67 mmol) and K2CO3 (0.41 g, 3.0 mmol) in DMF (10 mL) was heated at 130° C. for 4 h. The mixture was added to saturated aqueous NaHCO3 (50 mL), extracted with EtOAc (3×25 mL) and the combined organic phases dried over Na2SO4 and concentrated in vacuo. Purification by gradient column chromatography eluting with 0-45% EtOAc in hexane yielded the title compound (40 mg, 0.09 mmol).

Workup

  1. extractionextracted with EtOAc (3×25 mL)
  2. dry with materialthe combined organic phases dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by gradient column chromatography
  5. washeluting with 0-45% EtOAc in hexane

Sources & evidence

ORD record
ord-a0f86a5b90154379b85d43e00a9bb429
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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