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

HRID 332938Notes

Reaction equation

HRID 332938 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-4dc6eea7b698411d98ac5ef72a67e901
Source dataset
uspto-grants-2014_11
Patent number
US08877922B2

Reaction notes

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