O-Phenylenediamine → 6-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-N-(2-aminophenyl)hexanamide

HRID 251667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251667
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:12][N:13]=[CH:14][C:15]1[NH:19][C:18]([CH3:20])=[C:17]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29](O)=[O:30])=[O:22])[C:16]=1[CH3:32].Cl.C(N=C=NCCCN(C)C)C.O[C:46]1[C:54]2[N:53]=N[NH:51][C:50]=2[CH:49]=[CH:48][CH:47]=1.C(N(CC)CC)C.C1(N)C=CC=CC=1N>[Cl-].[Na+].O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:12][N:13]=[CH:14][C:15]1[NH:19][C:18]([CH3:20])=[C:17]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:51][C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:54]=2[NH2:53])=[O:30])=[O:22])[C:16]=1[CH3:32]

Komponenten

8

Edukt 5

HCID 7243O-PhenylenediamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1363879516-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 1363879546-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-N-(2-aminophenyl)hexanamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

6-(5-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamido)-hexanoic acid (441 mg, 1 mmol), and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxy-benzotriazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and o-phenylenediamine (432 mg, 4 mmol) were added. The mixture was stirred for 24 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 (430 mg, 81% yield) as a red solid. 1H NMR (DMSO-d6)δ1.38 (m, 2H, CH2), 1.54 (m, 2H, CH2), 1.62 (m, 2H, CH2), 2.30 (s, 3H, pyrrole-CH3), 2.32 (t, J=8.0 Hz, 2H, CH2CO), 2.41 (s, 3H, pyrrole-CH3), 3.22 (m, 2H, NCH2), 4.82 (s, 2H, benzene-NH2), 6.51 (t, J=8.0 Hz, 1H, Ar—H), 6.69 (d, J=8.0 Hz, 1H, Ar—H), 6.87 (m, 2H, Ar—H), 7.14 (d, J=8.0 Hz, 1H, Ar—H), 7.20 (m, 1H, Ar—H), 7.65 (t, J=4.0 Hz, 1H, CONH), 8.33 (dd, J=4.0 and 8.0 Hz, 1H, Ar—H), 8.63 (s, 1H, vinyl-H), 9.11 (s, 1H, benzene-NH), 10.73 (s, 1H, indolinone-NH), 11.82 (s, 1H, pyrrole-NH). LC-MS (m/z) 532 (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-4ce62858bf064d17b840673ad343e4bc
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863315B2

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