2-Thiophenecarbonyl chloride → HCID 178522594, Verbindung

HRID 555922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555922
[CH2:1]([NH:8][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([C:16]2[NH:20][N:19]=[N:18][N:17]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[C:35](Cl)=[O:36]>ClCCCl>[C:2]1([CH2:1][NH:8][C:9]2[N:14]=[C:13]([NH:15][C:35]([C:31]3[S:30][CH:34]=[CH:33][CH:32]=3)=[O:36])[C:12]([C:16]3[NH:17][N:18]=[N:19][N:20]=3)=[CH:11][N:10]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 789282-Thiophenecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 178508735HCID 178508735, Verbindung

Produkt 1

HCID 178522594HCID 178522594, VerbindungAusbeute 12,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of N2-Benzyl-5-(1H-tetrazol-5-yl)pyrimidine-2,4-diamine (27 mg, 0.1 mmol) in 1 mL of DCE, DIPEA (0.3 mmol, 3.0 eq.) was added followed by thiophene-2-carbonyl chloride (0.15 mmol, 1.5 eq.). The reaction was stirred at room temperature for 2 hours. The crude reaction mixture was concentrated down in vacuo, and the residue redissolved in ethylacetate. This organic solution was extracted several times with water, dried with magnesium sulfate, filtered and concentrated. The residue was purified by reverse phase HPLC to give 4.8 mg of the desired compound. 1H-NMR (400 MHz, d6-DMSO): δ 9.07 (t, 1H), 7.81 (dd, 1H), 7.77 (dd, 1H), 7.36-7.29 (m, 4H), 7.28-7.23 (m, 1H), 7.16 (t, 1H), 4.45 (d, 2H). MS (EI) for C17H14N8OS: 379 (M+H).

Aufarbeitung

  1. customThe crude reaction mixture
  2. concentrationwas concentrated down in vacuo
  3. dissolutionthe residue redissolved in ethylacetate
  4. extractionThis organic solution was extracted several times with water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f24f64ac25344978a1204289b413d221
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053454B2

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