Trifluoroacetic acid → 4-methyl-N-(3-morpholinophenyl)-3-(3-pyrrolidin-3-yloxybenzamido)benzamide

HRID 2415717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415717
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][CH2:18][CH:17]([O:20][C:21]2[CH:22]=[C:23]([CH:49]=[CH:50][CH:51]=2)[C:24]([NH:26][C:27]2[CH:28]=[C:29]([CH:45]=[CH:46][C:47]=2[CH3:48])[C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([N:39]3[CH2:44][CH2:43][O:42][CH2:41][CH2:40]3)[CH:34]=2)=[O:31])=[O:25])[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH3:48][C:47]1[CH:46]=[CH:45][C:29]([C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([N:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)[CH:34]=2)=[O:31])=[CH:28][C:27]=1[NH:26][C:24](=[O:25])[C:23]1[CH:49]=[CH:50][CH:51]=[C:21]([O:20][CH:17]2[CH2:18][CH2:19][NH:15][CH2:16]2)[CH:22]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 226361163-[3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzamido]-4-methyl-N-(3-morpholinophenyl)benzamide

Produkt 1

HCID 226361154-methyl-N-(3-morpholinophenyl)-3-(3-pyrrolidin-3-yloxybenzamido)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trifluoroacetic acid (0.6 ml) was added to a stirred solution of 3-[3-(1-tert-butoxycarbonylpyrrolidin-3-yloxy)benzamido]-4-methyl-N-(3-morpholinophenyl)benzamide (0.3 g) in methylene chloride (6 ml) which had been cooled to 0° C. The reaction mixture was stirred at ambient temperature for 3 hours. The mixture was evaporated and the residue was triturated under diethyl ether to give the title compound, as its trifluoroacetate salt. The solid so obtained was dissolved in water (15 ml) and basified by the addition of potassium carbonate. The resultant precipitate was collected, washed with water and dried under vacuum to give the title compound (0.18 g); NMR Spectrum: (DMSOd6) 1.76 (m, 1H), 2.02 (m, 1H), 2.23 (s, 3H), 2.83 (ml, 2H), 3.06 (m, 5H), 3.55 (m, 1H), 3.76 (t, 4H), 4.98 (m, 1H), 6.62 (d, 1H), 7.12 (m, 2H), 7.31 (d, 1H), 7.4 (m, 3H), 7.52 (m, 2H), 7.78 (d, 1H), 7.99 (s, 1H), 10.07 (s, 1H), 10.08 (s, 1H); Mass Spectrum: M+H+ 501.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was triturated under diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-cc751faaf3a2466295121e5d8fc724e7
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06821965B1

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