Water → HCID 72706724, compound

HRID 1474577Notes

Reaction equation

HRID 1474577 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[NH2:12].[S:13](Cl)(=[O:16])(=[O:15])[NH2:14].CCOC(C)=O.O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[NH:12][S:13]([NH2:14])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24499Chlorosulfamic acidHCID 91618718HCID 91618718, compound

Product 1

HCID 72706724HCID 72706724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-7-fluoro-2,3-dihydro-1H-inden-1-amine (CAS No. 1337690-24-0, 371 mg, 2.00 mmol) and TEA (0.697 mL, 5.00 mmol) in DCM (10 mL) was added sulfamoyl chloride (462 mg, 4.00 mmol) at 0° C. The reaction mixture was stirred for 3 hours at room temperature. To the reaction mixture were added AcOEt and water, and the layers were separated. The organic layer was washed with brine, dried over anhydrous Na2SO4. The solvent was concentrated in vacuo and the residue was purified by silicagel column chromatography (gradient 20% to 33% AcOEt in n-heptane) to afford the title compound (165 mg, 0.623 mmol) as a racemate.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue was purified by silicagel column chromatography (gradient 20% to 33% AcOEt in n-heptane)

Sources & evidence

ORD record
ord-b2790800537a44e09055653e17d04674
Source dataset
uspto-grants-2015_04
Patent number
US09018260B2

Reaction notes

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