Dimethylformamide → n-(2-Aminophenyl)-6-(2-(2-(((5-chloro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamide

HRID 1695064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695064
[Cl:1][C:2]1[CH:3]=[C:4]2C(=[CH:9][CH:10]=1)NC(=O)[C:5]2=[N:12][N:13]=CC1(C)CC(C)(C(O)=O)CN1.Cl.C(N=C=NCCCN(C)C)C.[OH:37][C:38]1C2N=NNC=2[CH:41]=[CH:40][CH:39]=1.C([N:49]([CH2:52][CH3:53])[CH2:50][CH3:51])C.[NH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[NH:61][C:62](=[O:73])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][NH2:72])=[N:65][CH:64]=1.[CH3:74][N:75]([CH:77]=[O:78])C>[Cl-].[Na+].O>[NH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[NH:61][C:62](=[O:73])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][NH:72][C:38]([C:39]2[C:40]([CH3:41])=[C:52]([CH:53]=[N:13][N:12]=[C:5]3[C:4]4[C:74](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)[NH:75][C:77]3=[O:78])[NH:49][C:50]=2[CH3:51])=[O:37])=[N:65][CH:64]=1

Komponenten

8

Edukt 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57993739N-(2-aminophenyl)-6-(2-aminoethylamino)nicotinamideHCID 1372525142-(((5-Chloro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 136647243n-(2-Aminophenyl)-6-(2-(2-(((5-chloro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)ethylamino)nicotinamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

2-(((5-Chloro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid (344 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (384 mg, 2 mmol), hydroxybenzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and N-(2-aminophenyl)-6-(2-aminoethylamino)nicotinamide (284 mg, 1.05 mmol) were added. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (376 mg, 63%) as a red solid. LC-MS (m/z) 598 (M+1).

Aufarbeitung

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7d10c4f79b9440b3a7cc5e0e53940346
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158656B2

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