Triethylamine → HCID 69351499, Verbindung

HRID 970752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970752
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:26])[CH:13]1[CH2:18][CH2:17][C:16]([C:19]2[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH2:14]1.C(N(CC)CC)C.O1CCOCC1>C(Cl)Cl>[ClH:8].[CH3:11][N:12]([CH3:26])[CH:13]1[CH2:18][CH2:17][C:16]([C:19]2[N:24]=[C:23]([NH:25][C:6](=[O:7])[C:5]3[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH2:14]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 678794-Fluorobenzoyl chlorideHCID 588523656-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine

Produkt 1

HCID 69351499HCID 69351499, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Combine 4-fluoro-benzoyl chloride (127 mg, 0.80 mmol), 6-(4-dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine, isomer 2 (preparation 11, 145 mg, 0.67 mmol), triethylamine (81 mg, 0.80 mmol) and 1,4-dioxane (6 mL) and heat at 55° C. for 15 hr. Dilute the mixture with DCM, wash with 0.1N NaOH solution. Extract the aqueous layer twice with DCM. Combine the organic layers, dry over sodium sulfate, filter and concentrate to give a residue. Purify the residue by chromatography (silica gel, 5% 2M NH3/MeOH in DCM) to provide the free amine of the title compound as a slightly yellow oil (183 mg, 80%): MS (ES): m/z=340.1 (M+H)+; 1H NMR (CDCl3): δ 8.55 (s, br, 1H), 8.19 (d, 1H), 7.95 (m, 2H), 7.73 (t, 1H), 7.18 (m, 2H), 6.66 (m, 1H), 2.73 (m, 1H), 2.47 (m, 3H), 2.37 (s, 6H), 2.15 (m, 2H), 1.57 (m, 1H). Using a salt formation method similar to that in example 1 gives the hydrochloride salt: hydrochloride salt: Anal. cal'd for C20H22FN3O.1.5HCl0.5H2O: C, 59.59; H, 6.13; N, 10.42. Found: C, 59.71; H, 5.56; N, 10.31.

Aufarbeitung

  1. washwash with 0.1N NaOH solution
  2. extractionExtract the aqueous layer twice with DCM
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give a residue
  7. customPurify the residue by chromatography (silica gel, 5% 2M NH3/MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-81b2e44be05143f5b51e0b2de013c010
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312236B2

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