Chlorosulfamic acid → (S)-2-sulfamoylamino-6-((1-butyrylpiperidin-3-yl)methoxy)benzonitrile

HRID 1483929Notes

Reaction equation

HRID 1483929 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:22])[CH2:19][CH2:20][CH3:21])[CH2:13]2)[C:3]=1[C:4]#[N:5].[S:23](Cl)(=[O:26])(=[O:25])[NH2:24]>CC(N(C)C)=O>[S:23]([NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:22])[CH2:19][CH2:20][CH3:21])[CH2:13]2)[C:3]=1[C:4]#[N:5])(=[O:26])(=[O:25])[NH2:24]

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 86714268(S)-2-amino-6-((1-butyrylpiperidin-3-yl)methoxy)benzonitrile

Product 1

HCID 86714267(S)-2-sulfamoylamino-6-((1-butyrylpiperidin-3-yl)methoxy)benzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of (S)-2-amino-6-((1-butyrylpiperidin-3-yl)methoxy)benzonitrile (Example 1b, 9.2 g, 30.53 mmol) in DMA (60 mL) was added sulfamoyl chloride (Example 1f, 10.54 g, 91.58 mmol) at room temperature under nitrogen. The reaction mixture was stirred at room temperature under nitrogen overnight then concentrated under reduced pressure, diluted with EtOAc, successively washed with NaHCO3, water and brine, dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound as colorless gel (9.5 g) in 82% yield. MS 381 (MH+).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washsuccessively washed with NaHCO3, water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8a66fca4db0349ccbce6c077d99ad44a
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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