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

HRID 1045202Notes

Reaction equation

HRID 1045202 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-31d0aae323294f12b9640c1ddc3b4640
Source dataset
uspto-grants-2013_10
Patent number
US08563735B2

Reaction notes

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