Dabco → HCID 21081524, Verbindung

HRID 347468

Reaktionsgleichung

Reaktionsgleichung von HRID 347468
[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[CH:32]=[CH:31][NH:30][C:26]=2[N:27]=[CH:28][N:29]=1.N12CCN(CC1)CC2>CC#N>[N:27]1[CH:26]2[NH:30][CH:31]=[CH:32][CH:25]2[C:24]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:9][C:10]([NH:12][C:13](=[O:22])[CH2:14][C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)=[S:11])=[CH:3][C:2]=2[F:1])=[N:29][CH:28]=1

Komponenten

5

Edukt 3

HCID 9237DabcoHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 210814951-(3-Fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea2×

Produkt 1

HCID 21081524HCID 21081524, VerbindungAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture 1-(3-fluoro-4-hydroxyphenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea (24 mg, 0.075 mmol, Compound A of Example 3), 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (11 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 reverse phase preparative HPLC to give the title compound (5.3 mg, 16%) as a white solid. 1H NMR (CDCl3) δ 12.46 (s, 1H), 8.48 (s, 1H), 8.44 (s, 1H), 7.95 (dd, 1H, J=11.6, 2.8 Hz), 7.43 (m, 1H), 7.34 (m, 1H), 7.29 (m, 4H), 7.13 (app. T, 2H, J=8.6 Hz), 6.80 (s, 1H), 3.72 (s, 2H); MS(ESI+) m/z 440 (M+H)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8f6be317b0d744058c2d8ae581720e44
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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