Mafenide → 2-(3-Cyano-phenoxy)-N-(4-sulfamoyl-benzyl)-nicotinamide

HRID 844051

Reaktionsgleichung

Reaktionsgleichung von HRID 844051
[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O)#[N:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH2:55][CH2:56][C:57]1[CH:62]=[CH:61][C:60]([S:63]([NH2:66])(=[O:65])=[O:64])=[CH:59][CH:58]=1>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[O:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([NH:55][CH2:56][C:57]1[CH:58]=[CH:59][C:60]([S:63](=[O:65])(=[O:64])[NH2:66])=[CH:61][CH:62]=1)=[O:11])#[N:2]

Komponenten

6

Edukt 4

HCID 3998MafenideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 128493352-(3-Cyano-phenoxy)-nicotinic acid

Produkt 1

HCID 226120732-(3-Cyano-phenoxy)-N-(4-sulfamoyl-benzyl)-nicotinamideAusbeute 40,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-Cyano-phenoxy)-nicotinic acid (0.140 g 0.600 mmole), BOP (0.260 grams, 0.600 mmole) and DIEA (0.310 μl, 1.8 mmole) in dimethylformamide (5 ml) was added 4-Aminomethyl-benzenesulfonamide (0.135 grams, 0.600 mmole) and stirred at room temperature over night. The reaction was quenched with water and extracted with ethyl acetate. The combined organics were washed with alternating portions of 5% citric acid and sat'd bicarb, dried over Na2SO4, filtered and concentrated to a product which was recrystalized from ethyl acetate to give a white solid (0.100 g). M.P. 179-180° C.; Anal. calcd. for C20H16N4O4S; C, 58.81; H, 3.95; N, 13.72. Found: C, 57.47; H, 4.15; N. 13.45.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were washed with alternating portions of 5% citric acid
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a product which
  7. customwas recrystalized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-95b0ae0cc4cf4406b73bb5dc768e9860
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380218B1

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