Triethylamine → HCID 10108897, Verbindung

HRID 1269372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269372
[Cl:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[O:16]1[C:21]2[CH:22]=[CH:23][C:24]([NH2:26])=[CH:25][C:20]=2[O:19][CH2:18][CH2:17]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:26][C:24]2[CH:23]=[CH:22][C:21]3[O:16][CH2:17][CH2:18][O:19][C:20]=3[CH:25]=2)[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 167664,6-dichloro-N-phenyl-1,3,5-triazin-2-amineHCID 891481,4-Benzodioxan-6-ylamine

Produkt 1

HCID 10108897HCID 10108897, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 4,6-dichloro-N-phenyl-[1,3,5]triazine-2-amine (95 mg, 0.39 mmoles) in tetrahydrofuran (2 ml) was added a solution of 1,4-benzodioxan-6-amine (64 mg, 0.42 mmoles) and triethylamine (0.07 ml, 0.50 mmoles) in tetrahydrofuran (0.5 ml). After stirring for 24 hours, the mixture was concentrated under vacuum and the residue was dissolved in ethyl acetate (10 ml). The solution was washed with a solution composed of saturated aqueous sodium chloride solution and 1 M hydrochloric acid (1:1, 2×10 ml), dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate-hexanes to provide CT-32028 (97 mg, 69% yield). 1H NMR (d6-DMSO) δ 9.88–10.28 (m, 2H), 7.60–7.85 (m, 2H), 7.20–7.40 (m, 3H), 6.96–7.10 (m, 2H), 6.77–6.81 (m, 1H), 4.21 (s, 4H).

Aufarbeitung

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  3. washThe solution was washed with a solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate-hexanes
  8. customto provide CT-32028 (97 mg, 69% yield)

Quellen und Nachweise

ORD-Eintrag
ord-e5c12e355c6e4d02bb848f034360030d
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199238B2

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