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Propyl isocyanate → 4''-{3-Butyl-1-[2-chloro-5-(3-propyl-ureido)-phenyl]-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl}-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

HRID 36255
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 36255
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:44])=[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27](=[O:39])(=[O:38])[NH:28][C:29](=[O:37])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])=[CH:17][CH:16]=3)[C:10]([CH2:40][CH2:41][CH2:42][CH3:43])=[N:9]2)[CH:7]=1.[CH2:45]([N:48]=[C:49]=[O:50])[CH2:46][CH3:47]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:40]([C:10]1[N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:38])(=[O:39])[NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:19][CH:20]=2)[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:49]([NH:48][CH2:45][CH2:46][CH3:47])=[O:50])[CH:3]=[CH:4][C:5]=2[Cl:44])[N:9]=1)[CH2:41][CH2:42][CH3:43]
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Komponenten

5

Edukt 2

HCID 61033Propyl isocyanateHCID 100321934''-[1-(5-Amino-2-chloro-phenyl)-3-butyl-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

Produkt 1

HCID 102594114''-{3-Butyl-1-[2-chloro-5-(3-propyl-ureido)-phenyl]-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl}-biphenyl-2-sulfonic acid 2-chloro-benzoylamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 1049PyridineLösungsmittel

Versuchsvorschrift

At room temperature, under N2, a solution of 34 mg (0.052 mmole) of 2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 60), 6.4 mg (0.052 mmole) of DMAP, 23 mg (0.26 mmole) of propyl isocyanate, and 1 mL of pyridine was stirred overnight. After quenching with water, the organic material was extracted with EtOAc, washed with water and brine, and dried over sodium sulfate. The crude product obtained after filtration and removal of volatiles was flash chromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2) to give 23 mg (61%) of the desired compound as a white solid, mp >208° C. (gradual), homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 773 (M+K)+.

Aufarbeitung

  1. customAfter quenching with water
  2. extractionthe organic material was extracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product obtained
  6. filtrationafter filtration and removal of volatiles
  7. customchromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-432505845fda4bc2b35b9c1ceb2e42c0
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05411980

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