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

HRID 1695034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695034
[F: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:74])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][CH2:72][NH2:73])=[N:65][CH:64]=1.[CH3:75][N:76]([CH:78]=[O:79])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:74])[C:63]1[CH:68]=[CH:67][C:66]([NH:69][CH2:70][CH2:71][CH2:72][NH:73][C:38]([C:39]2[C:40]([CH3:41])=[C:52]([CH:53]=[N:13][N:12]=[C:5]3[C:4]4[C:75](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=4)[NH:76][C:78]3=[O:79])[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 57993723N-(2-aminophenyl)-6-(3-aminopropylamino)nicotinamideHCID 1372525122-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 136651723n-(2-Aminophenyl)-6-(3-(2-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)-methyl)-3,5-dimethyl-1h-pyrrole-4-carboxamido)propylamino)nicotinamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

2-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-4-carboxylic acid (328 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-(3-aminopropylamino)nicotinamide (299 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 (452 mg, 76%) as a red solid. 1H NMR (DMSO-d6)δ1.78 (m, 2H, CH2), 2.36 (s, 3H, pyrrole-CH3), 2.45 (s, 3H, pyrrole-CH3), 3.30 (m, 2H, CH2), 3.38 (m, 2H, CH2), 4.85 (s, 2H, benzene-NH2), 6.51 (m, 1H), 6.57 (m, 1H), 6.75 (d, J=8.0 Hz, 1H), 6.85 (m, 1H), 6.93 (m, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.20 (m, 2H), 7.71 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 8.34 (d, J=8.0 Hz, 1H), 8.64 (s, 2H), 9.37 (s, 1H, benzene-NH), 10.74 (s, 1H, indolinone-NH), 11.85 (s, 1H, pyrrole-NH). LC-MS (m/z) 596 (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-1dd411ad12ef427f81638ddf73000c90
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158656B2

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