Dabco → HCID 21081494, Verbindung

HRID 347467

Reaktionsgleichung

Reaktionsgleichung von HRID 347467
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13](=[O:22])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[S:11])[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:24]1[C:25]2[S:32][CH:31]=[C:30]([CH3:33])[C:26]=2[N:27]=[CH:28][N:29]=1.N12CCN(CC1)CC2>CC#N>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13](=[O:22])[CH2:14][C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[S:11])[CH:5]=[CH:6][C:7]=1[O:8][C:24]1[CH:25]2[S:32][CH:31]=[C:30]([CH3:33])[CH:26]2[N:27]=[CH:28][N:29]=1

Komponenten

5

Edukt 3

HCID 9237DabcoHCID 27775864-Chloro-7-methylthieno(3,2-d)pyrimidineHCID 21081495HCID 21081495, Verbindung2×

Produkt 1

HCID 21081494HCID 21081494, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 1-(3-fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea (24 mg, 0.075 mmol, Compound A of Example 3), 4-chloro-7-methylthieno[3,2-d]pyrimidine (13.8 mg, 0.075 mmol, commercially available) and 1,4-diazabicyclo[2.2.2]octane (DABCO, 8.4 mg, 0.075 mmol) was added MeCN (2 mL). The reaction was stirred at RT for 4 h and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC to give the title compound (11.2 mg, 31%) as a white solid. 1H NMR (CDCl3) δ 12.45 (s, 1H), 8.79 (s, 1H), 8.61 (s, 1H), 7.93 (dd, 1H, J=13.8, 2.2 Hz), 7.46 (s, 1H), 7.43 (m, 1H), 7,28 (m, 3H), 7.12 (m, 2H), 3.72 (s, 2H), 2.51 (s, 3H); MS(ESI+) m/z 471 (M+H)+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bc78f8683598467da20f522712729387
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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