Ethanol → HCID 178486159, Verbindung

HRID 1190138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190138
[C:1]1([C:7]2[CH:12]=[C:11]([CH2:13][CH2:14][S:15](=[O:20])(=[O:19])[N:16]([CH3:18])[CH3:17])[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[N:25](COCC[Si](C)(C)C)[CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CCO.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[C:11]([CH2:13][CH2:14][S:15](=[O:19])(=[O:20])[N:16]([CH3:17])[CH3:18])[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[NH:25][CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 887MethanolHCID 6422Trifluoroacetic acidHCID 589944524-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-dimethylsulfamoyl-ethyl)-phenyl]-amide

Produkt 1

HCID 178486159HCID 178486159, VerbindungAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 660 mg (1.19 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2-dimethylsulfamoyl-ethyl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (30 mL) was treated with EtOH (600 μL) and TFA (3 mL) and stirred at RT for 24 h. MeOH (20 mL) was added, and the solvents were evaporated in vacuo. The solid was triturated with acetonitrile to afford 342 mg (67%) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): δ 8.20-8.09 (m, 1H), 7.92 (s, 1H), 7.24-7.16 (m, 1H), 7.13 (s, 1H), 5.84-5.75 (m, 1H), 3.30-3.19 (m, 4H), 3.08-2.96 (m, 2H), 2.82 (s, 6H), 2.29-2.17 (m, 4H), 1.85-1.68 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C21H25N5O3S, 428.2 (M+H). found 428.1.

Aufarbeitung

  1. customthe solvents were evaporated in vacuo
  2. customThe solid was triturated with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-572a115631124b4b8b4d9cc5ff218d04
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674100B2

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