Diisopropylethylamine → 3-Chloro-n-{[trans-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}-4-(methylsulfonyl)thiophene-2-carboxamide

HRID 1172332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172332
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([N+:15]([O-:17])=[O:16])[CH2:13][C:12]([CH2:18][NH2:19])=[CH:11][CH2:10]1.[Cl:20][C:21]1[C:25]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][S:23][C:22]=1[C:30](Cl)=[O:31].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:20][C:21]1[C:25]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][S:23][C:22]=1[C:30]([NH:19][CH2:18][C:12]1[CH2:13][C@@H:14]([N+:15]([O-:17])=[O:16])[C@H:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH2:10][CH:11]=1)=[O:31]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27357753-Chloro-4-(Methylsulfonyl)Thiophene-2-Carbonyl ChlorideHCID 68769505[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl amine

Produkt 1

HCID 687719313-Chloro-n-{[trans-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}-4-(methylsulfonyl)thiophene-2-carboxamideAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Example 12C (33 mg, 0.11 mmol) in CH2Cl2 (1 mL), 3-chloro-4-methanesulfonyl-thiophene-2-carbonyl chloride (43 mg, 0.16 mmol) and diisopropylethyl amine (0.05 mL, 0.33 mmol) were added. The reaction mixture was stirred at room temperature overnight. It was concentrated under reduced pressure and purified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (48 mg, 84%). 1H NMR (300 MHz, CDCl3) δ ppm 8.39 (s, 1H), 8.19 (s, 1H), 7.40 (s, 1H), 7.17-7.25 (m, 2H), 5.82 (m, 1H), 5.04-5.17 (m, 1H), 3.98-4.19 (m, 3H), 3.18-3.21 (m, 3H), 2.51-2.95 (m, 3H), 2.16-2.35 (m, 1H). MS (ESI) m/z 523 (M+H)+.

Aufarbeitung

  1. concentrationIt was concentrated under reduced pressure
  2. custompurified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-0db8ceac46db43ccb9b4208a3e3596fe
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834012B2

Notizen zur Reaktion

Wird geladen…