Methylene-(2-morpholin-4-yl-ethyl)-amine → 4-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid 4-fluoro-benzylamide

HRID 2214696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214696
CC1(C)[O:6][C:5](=[CH:7][C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:9])[C:4](=[O:19])O1.[CH2:21]=[N:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CO>[F:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][NH:10][C:8]([C:7]2[CH2:21][N:22]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:4](=[O:19])[C:5]=2[OH:6])=[O:9])=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 15174513Methylene-(2-morpholin-4-yl-ethyl)-amineHCID 696563162-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-acetamide

Produkt 1

HCID 547046924-Hydroxy-1-(2-morpholin-4-yl-ethyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid 4-fluoro-benzylamideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-acetamide (77 mg, 0.275 mmol) and a 0.2 mmol solution of methylene-(2-morpholin-4-yl-ethyl)-amine in methanol (1.5 mL, 0. mmol) was heated at 70° C. for 1 h. The reaction mixture was cooled to room temperature and purified by preparative HPLC using methanol/water (0.1% TFA) as the eluent. The fractions containing the product were combined and concentrated to give the title compound as a pale yellow powder (42 mg, 32% yield). 1H NMR (500 MHz, DMSO) δ: 11.92 (1H, br s), 9.48 (1H, br s), 7.95 (1H, t, J=4.9 Hz), 7.34–7.31 (2H, m), 7.17–7.13 (2H, m), 4.42 (2H, d, J=4.9 Hz), 4.04 (2H, s), 4.01–3.95 (2H, m), 3.80–3.77 (2H, m), 3.66–3.39 (6H, m), 3.15–3.06 (2H, m). HRMS calcd for C18H21FN3O4 (M+H): 362.1516. found: 362.1505.

Aufarbeitung

  1. custompurified by preparative HPLC
  2. additionThe fractions containing the product
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-05fa39d853cd4f31acb57dd307457d6b
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109186B2

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