Chlorosulfamic acid → ((2-cyano-3-(sulfamoylamino)phenoxy)methyl)-N-ethylpiperidine-1-carboxamide

HRID 1483965Notes

Reaction equation

HRID 1483965 reaction equation
[NH2:1][C:2]1[C:3]([C:21]#[N:22])=[C:4]([CH:18]=[CH:19][CH:20]=1)[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][CH3:17])=[O:14].[S:23](Cl)(=[O:26])(=[O:25])[NH2:24]>CC(N(C)C)=O>[C:21]([C:3]1[C:2]([NH:1][S:23](=[O:26])(=[O:25])[NH2:24])=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][CH3:17])=[O:14])#[N:22]

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acidHCID 867142962-((3-amino-2-cyanophenoxy)methyl)-N-ethylpiperidine-1-carboxamide

Product 1

HCID 86714295((2-cyano-3-(sulfamoylamino)phenoxy)methyl)-N-ethylpiperidine-1-carboxamideYield 117.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-((3-amino-2-cyanophenoxy)methyl)-N-ethylpiperidine-1-carboxamide (Example 26b, 0.407 g, 1.35 mmol) in DMA (5 mL) was added sulfamoyl chloride (0.234 mg, 2.02 mmol) and the reaction mixture was stirred vigorously at r.t. for 2 h, then extracted with H2O/EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by Biotage purification system (120 g Silicycle column, DCM:THF=4:1 as eluent) to provide the desired product (0.606 g, 90%). MS 382 (MH+).

Workup

  1. extractionextracted with H2O/EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by Biotage purification system (120 g Silicycle column, DCM:THF=4:1 as eluent)

Sources & evidence

ORD record
ord-37a1f5d635dc4e14929b3b7dcb033a51
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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