1,2-Diiodoethane → N-[1-(2-phenylethyl)-5-iodo-4-ethoxycarbonylpyrazol-3-yl]-N-((2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))-biphenyl-4-yl)methyl]-n-propylamine

HRID 863712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 863712
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CCCC[CH2:10][CH3:11].C1([CH2:18][CH2:19][N:20]2[C:24](Br)=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]([N:31]([CH2:69][CH2:70][CH3:71])[CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[C:45]4[N:49]([C:50]([C:63]5[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=5)([C:57]5[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=5)[C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)[N:48]=[N:47][N:46]=4)=[CH:35][CH:34]=3)=[N:21]2)C=CC=CC=1.C(=O)=O.CC(C)=O.[I:79]CCI.[Cl-].[NH4+]>C1COCC1>[C:4]1([CH2:18][CH2:19][N:20]2[C:24]([I:79])=[C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:22]([N:31]([CH2:69][CH2:70][CH3:71])[CH2:32][C:33]3[CH:34]=[CH:35][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=4[C:45]4[N:49]([C:50]([C:51]5[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=5)([C:57]5[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=5)[C:63]5[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=5)[N:48]=[N:47][N:46]=4)=[CH:37][CH:38]=3)=[N:21]2)[CH:11]=[CH:10][CH:1]=[CH:2][CH:3]=1

Komponenten

7

Edukt 5

HCID 122241,2-DiiodoethaneHCID 25517Ammonium ChlorideHCID 18522661Acetone cardiceHCID 22103828N-[1-(2-phenylethyl)-4-ethoxycarbonyl-5-bromopyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamineHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 88329917N-[1-(2-phenylethyl)-5-iodo-4-ethoxycarbonylpyrazol-3-yl]-N-((2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))-biphenyl-4-yl)methyl]-n-propylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

0.18 ml of 1.6M n-butyl lithium/hexane solution were added to THF solution (10 ml) of 202 mg of N-[1-(2-phenylethyl)-5-bromo-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl(1H-tetrazol-5-yl))biphenyl-4-yl)methyl]-n-propylamine, while cooling with dry ice-acetone. After stirred for 2 hours, 667 mg of 1,2-diiodoethane were added thereto. After stirred for one hour, the mixture was then stirred at room temperature for further one hour. 10 ml of aqueous ammonium chloride solution were added to the reaction solution, THF was distilled off under reduced pressure, and the resultant was extracted with 50 ml of dichloromethane. After dried over magnesium sulfate, this was subjected to silica gel column chromatography (n-hexane-ethyl acetate=5:1) to obtain 84 mg of the intended compound as a pale red, amorphous solid.

Aufarbeitung

  1. stirringAfter stirred for one hour
  2. stirringthe mixture was then stirred at room temperature for further one hour
  3. distillationwas distilled off under reduced pressure
  4. extractionthe resultant was extracted with 50 ml of dichloromethane
  5. dry with materialAfter dried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-0253cc890b1146688070eb7d30169f9c
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721264

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