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

HRID 844051

반응식

HRID 844051 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 226120732-(3-Cyano-phenoxy)-N-(4-sulfamoyl-benzyl)-nicotinamide수율 40.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-95b0ae0cc4cf4406b73bb5dc768e9860
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380218B1

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