Hydrochloric Acid → HCID 86721869, compound

HRID 1049012Notes

Reaction equation

HRID 1049012 reaction equation
[CH:1]1([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.Cl>C(Cl)Cl>[CH:1]1([N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=2)[S:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 61778890HCID 61778890, compound

Product 1

HCID 86721869HCID 86721869, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclobutyl-(3-fluoro-phenyl)-amine (447 mg, 2.7 mmol) in DCM (8 mL) was added pyridine (438 μL, 5.4 mmol) followed by 4-fluorobenzenesulfonyl chloride (633 mg, 3.3 mmol) in DCM (3 mL) and then the reaction was stirred at room temperature for 2 hrs. The reaction was left to stand at room temperature for 64 hours. 1 M aqueous HCl was added then extracted with DCM, filtered through a phase separator and then purified by silica gel column chromatography (0-50% DCM in cyclohexane) to give N-cyclobutyl-4-fluoro-N-(3-fluoro-phenyl)-benzenesulfonamide (756 mg, 2.3 mmol, 85%). LCMS (m/z, Method A) ES+ 324 [M+1]+.

Workup

  1. waitThe reaction was left
  2. waitto stand at room temperature for 64 hours
  3. extractionthen extracted with DCM
  4. filtrationfiltered through a phase separator
  5. custompurified by silica gel column chromatography (0-50% DCM in cyclohexane)

Sources & evidence

ORD record
ord-32cd42efe44d424a802a471ee96c910e
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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