Pyridine → HCID 17981729, compound

HRID 2252021Notes

Reaction equation

HRID 2252021 reaction equation
N1C=CC=CC=1.[CH3:7][N:8]([O:19][CH3:20])[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH2:17])[CH:11]=1.[CH:21]([S:24](Cl)(=[O:26])=[O:25])([CH3:23])[CH3:22].CCCCCC>ClCCl.C(OCC)(=O)C>[CH3:7][N:8]([O:19][CH3:20])[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([NH:17][S:24]([CH:21]([CH3:23])[CH3:22])(=[O:26])=[O:25])[CH:11]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8058HexaneHCID 824082-Propanesulfonyl chlorideHCID 11513923HCID 11513923, compound

Product 1

HCID 17981729HCID 17981729, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add dry pyridine (234 mL, 2.94 moles) to a cold (0° C.) solution of N-[methyl] N-[methoxy] 3,4-diaminobenzamide (135 g, 0.69 moles) in 1 liter of dry dichloromethane under a nitrogen atomosphere. Add isopropylsulfonyl chloride (85.4 mL, 0.76 moles) at 0° C. over 30 minutes, stir the mixture 0° C. for another 30 minutes, and then at room temperature overnight. Concentrate the reaction mixture under reduced pressure and partition the residue with diethyl ether (1 L) and 5 N hydrochloric acid (1 L). Separate the layers, discard the diethyl ether layer, add ethyl acetate (1.5 L) to the aqueous layer and stir while adding solid sodium carbonate until pH=6.5. Extract the aqueous layer using ethyl acetate, wash the combined organic layers, dry over magnesium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography eluting with a gradient 65:3 ethyl acetate:hexane to 100% ethyl acetate to provide a 40% yield of the desired compound.

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationConcentrate the reaction mixture under reduced pressure
  4. custompartition the residue with diethyl ether (1 L) and 5 N hydrochloric acid (1 L)
  5. customSeparate the layers
  6. additionadd ethyl acetate (1.5 L) to the aqueous layer
  7. stirringstir
  8. additionwhile adding solid sodium carbonate until pH=6.5
  9. extractionExtract the aqueous layer
  10. washwash the combined organic layers
  11. dry with materialdry over magnesium sulfate
  12. concentrationconcentrate under reduced pressure
  13. washeluting with a gradient 65:3 ethyl acetate

Sources & evidence

ORD record
ord-94c68c31adcb4f469104582a39ca4848
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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