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Propyl chloroformate → (3-{3-Butyl-4-[2''-(2-chloro-benzoylsulfamoyl)-biphenyl-4-ylmethyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-4-chloro-phenyl)-carbamic acid propyl ester

HRID 36254
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 36254
[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.Cl[C:46]([O:48][CH2:49][CH2:50][CH3:51])=[O: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:46]([O:48][CH2:49][CH2:50][CH3:51])=[O:47])[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 7998Propyl chloroformateHCID 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 10010207(3-{3-Butyl-4-[2''-(2-chloro-benzoylsulfamoyl)-biphenyl-4-ylmethyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-4-chloro-phenyl)-carbamic acid propyl esterAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

At room temperature, under N2, a solution of 20 mg (0.031 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), 3.8 mg (0.031 mmole) of DMAP, 18.9 mg (0.154 mmole) of propyl chloroformate, and 1 mL pyridine was stirred overnight. After quenching with methanol and 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 15 mg (65%) of the desired compound as a white solid, mp >119° C. (gradual), homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 736 (M+1)+.

Aufarbeitung

  1. customAfter quenching with methanol and 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-2ed56beeec4340a8b46c668a07cf5fec
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05411980

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