Trifluoroacetic acid → HCID 11634981, Verbindung

HRID 1714678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1714678
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]3)[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.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl.CCO>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[NH:28][C:27]([C:29]#[N:30])=[CH:26][N:25]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 59128589HCID 59128589, Verbindung

Produkt 1

HCID 11634981HCID 11634981, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-methoxy-piperidin-4-yl)-phenyl]-amide (as prepared in previous step, 31 mg, 0.020 mmol) in DCM (0.5 mL) and EtOH (11 μL) was added TFA (0.1 mL). The resulting solution was stirred at RT for 6 h. The reaction mixture was concentrated in vacuo and the resulting residue was dried for 1 h, suspended in ether (10 mL) and sonicated for 5 min. The solid formed was collected by suction filtration to obtain the title compound (17.3 mg, 58%). 1H-NMR (DMSO; 400 MHz): δ 9.70 (s, 1H), 8.30 (s, 1H), 7.83 (d, 1H, J=8.4 Hz), 7.14 (d, 1H, J=8.4 Hz), 7.05 (s, 1H), 5.71 (br s, 1H), 3.30-3.55 (m, 5H), 2.41-2.62 (m, 2H), 2.12-2.19 (m, 4H), 1.60-1.85 (m, 8H). Mass spectrum (ESI, m/z): Calcd. for C23H27N5O2, 406.2 (M+H), found 406.1.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was dried for 1 h
  3. customsonicated for 5 min
  4. customThe solid formed
  5. filtrationwas collected by suction filtration

Quellen und Nachweise

ORD-Eintrag
ord-0e43b6cca9414dad8ae21a4e39f4f07a
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795279B2

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