Pyridine → (R)-tert-butyl-2-((2-cyano-3-(sulfamoylamino)phenoxy)methyl)piperidine-1-carboxylate

HRID 2280140Notes

Reaction equation

HRID 2280140 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[C:17]=1[C:23]#[N:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[S:31](Cl)(=[O:34])(=[O:33])[NH2:32].C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][S:31](=[O:34])(=[O:33])[NH2:32])[C:17]=1[C:23]#[N:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 24499Chlorosulfamic acidHCID 516892Sodium BicarbonateHCID 86714286(R)-tert-butyl-2-((3-amino-2-cyanophenoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 86714285(R)-tert-butyl-2-((2-cyano-3-(sulfamoylamino)phenoxy)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of (R)-tert-butyl-2-((3-amino-2-cyanophenoxy)methyl)piperidine-1-carboxylate (Example 15d, 8.65 g. 26.1 mmol) in dimethyl acetamide (48 mL) were added pyridine (8.44 mL, 104 mmol) and sulfamoyl chloride (6.03 g. 52.2 mmol). The reaction mixture was stirred at room temperature for 1 hour, neutralized with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound as a clear oil, which was used immediately in the next step. MS 311 (MH+-boc).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a2aa3613355145c99d2dcbbb9bf68920
Source dataset
uspto-grants-2015_09
Patent number
US09138013B2

Reaction notes

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