Diisopropylethylamine → 3-cyano-4-((tetrahydro-2H-pyran-4-yl)methylamino)benzenesulfonamide

HRID 1520647Notes

Reaction equation

HRID 1520647 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[O:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>O1CCCC1.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[NH:21][CH2:20][CH:17]1[CH2:18][CH2:19][O:14][CH2:15][CH2:16]1)#[N:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27732104-AminomethyltetrahydropyranHCID 251398973-Cyano-4-fluorobenzene-1-sulfonamide

Product 1

HCID 671265013-cyano-4-((tetrahydro-2H-pyran-4-yl)methylamino)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Cyano-4-fluorobenzenesulfonamide (500 mg), (tetrahydropyran-4-yl)methylamine (288 mg), and N,N-diisopropylethylamine (1.3 mL) were heated at 80° C. in tetrahydrofuran (15 mL) overnight. The mixture was diluted with ethyl acetate, washed with NaHCO3 solution and brine, and dried (Na2SO4), filtered and concentrated. The product was triturated from ethyl acetate.

Workup

  1. washwashed with NaHCO3 solution and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was triturated from ethyl acetate

Sources & evidence

ORD record
ord-8ac759f32af9486196001fe9cfaa9139
Source dataset
uspto-grants-2015_07
Patent number
US09073855B2

Reaction notes

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