1-Hydroxybenzotriazole → N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-tetrahydrofuran-3-yloxybenzamide

HRID 967913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967913
Cl.CN(C)CCCN=C=NCC.[O:13]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=O)[CH2:14]1.ON1C2C=CC=CC=2N=N1.[NH2:38][C:39]1[CH:40]=[C:41]([NH:46][C:47](=[O:60])[C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([N:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)[CH:49]=2)[CH:42]=[CH:43][C:44]=1[CH3:45]>CN(C=O)C.O>[CH3:45][C:44]1[CH:43]=[CH:42][C:41]([NH:46][C:47](=[O:60])[C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([N:54]3[CH2:55][CH2:56][O:57][CH2:58][CH2:59]3)[CH:49]=2)=[CH:40][C:39]=1[NH:38][C:22](=[O:24])[C:21]1[CH:25]=[CH:26][CH:27]=[C:19]([O:18][CH:15]2[CH2:16][CH2:17][O:13][CH2:14]2)[CH:20]=1

Komponenten

7

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamideHCID 222910893-(Tetrahydrofuran-3-yloxy)benzoic acid

Produkt 1

HCID 22291058N-[2-methyl-5-(3-morpholinobenzamido)phenyl]-3-tetrahydrofuran-3-yloxybenzamideAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.165 g) was added to a stirred mixture of 3-(tetrahydrofuran-3-yloxy)benzoic acid (0.15 g), 1-hydroxybenzotriazole (0.146 g) and DMF (5 ml) which had been cooled to 0° C. The reaction mixture was stirred at 0° C. for 5 minutes and a solution of N-(3-amino-4-methylphenyl)-3-morpholinobenzamide (0.224 g) in DMF (1 ml) was added. The reaction mixture was allowed to come to ambient temperature and was stirred for 16 hours. The reaction mixture was poured into water and the resultant solid was isolated and purified by column chromatography on silica using a 99:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.228 g); NMR Spectrum: (DMSOd6) 1.99 (m, 1H), 2.18 (s, 3H), 2.25 (m, 1H), 3.17 (t, 4H), 3.72 (t, 4H), 3.88 (m, 4H), 5.13 (m, 1H), 7.11 (m, 2H), 7.21 (d, 1H), 7.39 (m, 5H), 7.56 (m, 2H), 7.79 (m, 2H), 9.83 (s, 1H), 10.11 (s, 1H); Mass Spectrum: M+H+ 502.

Aufarbeitung

  1. customto come to ambient temperature
  2. stirringwas stirred for 16 hours
  3. customthe resultant solid was isolated
  4. custompurified by column chromatography on silica using
  5. additiona 99:1 mixture of methylene chloride and methanol as eluent

Quellen und Nachweise

ORD-Eintrag
ord-c62d76b5e5824b0cbe9b6dc38fdb56ea
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956037B2

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