Diisopropylethylamine → 1-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid 4'-[bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamide

HRID 39180

Reaktionsgleichung

Reaktionsgleichung von HRID 39180
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)([CH3:24])[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH2:23])[CH:17]=3)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[O:33]1[C:37]2[CH:38]=[CH:39][C:40]([C:42]3([C:45](O)=[O:46])[CH2:44][CH2:43]3)=[CH:41][C:36]=2[O:35][CH2:34]1.CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)([CH3:24])[C:10]2[CH:11]=[CH:12][C:13]([C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH:23][C:45]([C:42]4([C:40]5[CH:39]=[CH:38][C:37]6[O:33][CH2:34][O:35][C:36]=6[CH:41]=5)[CH2:44][CH2:43]4)=[O:46])[CH:17]=3)=[CH:14][CH:15]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acidHCID 671206764'-[Bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamine

Produkt 1

HCID 671206751-Benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid 4'-[bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

4′-[Bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamine (˜10 mmol) and 1-benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid (2.28 g, 11 mmol) were dissolved in chloroform (25 mL) followed by addition of TCPH (4.1 g, 12 mmol) and DIEA (5.0 mL, 30 mmol). The reaction mixture was heated at 65° C. for 48 h. The volatiles were removed under reduced pressure. The residue was distributed between water (200 mL) and ethyl acetate (150 mL). The organic layer was washed with 5% NaHCO3 (2×150 mL), water (1×150 mL), brine (1×150 mL) and dried over MgSO4. Evaporation of the solvent yielded crude 1-benzo[1,3]dioxol-5-yl-cyclopropanecarboxylic acid 4′-[bis-(4-methoxyphenyl)-methylsulfanyl]-6-methylbiphenyl-3-ylamide as a pale oil, which was used without further purification. ESI-MS m/z calc. 629.0, found 630.0 (M+1) (HPLC purity ˜85-90%, UV254 nm).

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. washThe organic layer was washed with 5% NaHCO3 (2×150 mL), water (1×150 mL), brine (1×150 mL)
  3. dry with materialdried over MgSO4
  4. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-00d92a98754e46dd90deba1e842a19d2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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