Triethylamine → N-[(2-{3-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetyl]-methanesulfonamide

HRID 11612

Reaktionsgleichung

Reaktionsgleichung von HRID 11612
[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C@@H:12]([CH3:13])[CH2:11][N:10]([C:14](=[O:29])[CH2:15][CH2:16][C:17]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:18]=3[O:19][CH2:20][C:21](O)=[O:22])[C@H:9]([CH3:30])[CH2:8]2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[CH3:45][S:46]([NH2:49])(=[O:48])=[O:47].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C@@H:12]([CH3:13])[CH2:11][N:10]([C:14](=[O:29])[CH2:15][CH2:16][C:17]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:18]=3[O:19][CH2:20][C:21]([NH:49][S:46]([CH3:45])(=[O:48])=[O:47])=[O:22])[C@H:9]([CH3:30])[CH2:8]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69656021(2-{3-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetic Acid

Produkt 1

HCID 69655596N-[(2-{3-[4-(4-Fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetyl]-methanesulfonamideAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of (2-{3-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-3-oxo-propyl}-5-methyl-phenoxy)-acetic acid (0.052 g, 0.12 mmol) in methylene chloride (1 mL) was added 4-dimethylaminopyridine (0.022 g, 0.18 mmol), (3-(dimethylamino)propyl)ethyl carbodiimide hydrochloride (0.032 g, 0.17 mmol), methanesulfonamide (0.015 g, 0.16 mmol) and triethylamine (0.035 mL, 0.25 mmol). The reaction was stirred at ambient temperature for 18 hours. The reaction mixture was then diluted with dichloromethane and washed with 0.2 M aqueous hydrochloric acid. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by trituration in methylene chloride/diethyl ether/hexanes to give the title compound (0.050 g, LRMS: 520.3).

Aufarbeitung

  1. washwashed with 0.2 M aqueous hydrochloric acid
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by trituration in methylene chloride/diethyl ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7c1427aeb6c74cd89a227305147d78b4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098212B2

Verknüpfte Notizen

Wird geladen…