2,4,6-Trifluorobenzoyl chloride → HCID 69351067, Verbindung

HRID 970747

Reaktionsgleichung

Reaktionsgleichung von HRID 970747
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]([Cl:6])=[O:5].[CH3:13][N:14]([CH3:28])[CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[N:26]=[C:25]([NH2:27])[CH:24]=[CH:23][CH:22]=2)=[CH:17][CH2:16]1>N1C=CC=CC=1.Cl>[ClH:6].[ClH:6].[CH3:13][N:14]([CH3:28])[CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[N:26]=[C:25]([NH:27][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][C:9]([F:11])=[CH:8][C:7]=3[F:12])[CH:24]=[CH:23][CH:22]=2)=[CH:17][CH2:16]1

Komponenten

5

Edukt 2

HCID 1448952,4,6-Trifluorobenzoyl chloride2×HCID 588523656-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine

Produkt 1

HCID 69351067HCID 69351067, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Add 2,4,6-trifluorobenzoyl chloride (117 mg, 0.60 mmol) to a solution of 6-(4-dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine, isomer 1 (preparation 10, 100 mg, 0.46 mmol) in pyridine (6 mL) and heat at 55° C. overnight. Re-add another portion of 2,4,6-trifluorobenzoyl chloride (50 mg, 0.26 mmol) and heat at 65° C. for 4 hr. Remove volatiles under reduced pressure, dissolve the residue in 1N HCl, extract twice with ethyl ether. Adjust aqueous layer to pH>11 with 5N NaOH. Extract the aqueous layer there times with DCM. Combine 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 colorless oil (84 mg, 49%): MS (ion spray): m/z=376.2 (M+H)+; 1H NMR (CDCl3): δ 8.91 (s, br, 1H), 8.20 (d, 1H), 7.73 (t, 1H), 7.14 (d, 1H), 6.71 (m, 2H), 6.61 (m, 1H), 2.65 (m, 1H), 2.44 (m, 3H), 2.35 (s, 6H), 2.12 (m, 2H), 1.53 (m, 1H). Using a salt formation method similar to that in example 1 provides the di-hydrochloride salt. Di-hydrochloride salt: Anal. cal'd for C20H20F3N3O.2HCl: C, 53.58; H, 4.95; N, 9.37. Found: C, 53.42; H, 4.91; N, 9.23.

Aufarbeitung

  1. extractionextract twice with ethyl ether
  2. extractionExtract the aqueous layer there times with DCM
  3. dry with materialCombine organic layers, dry 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-a40fa0fc19924724b828155c59d974c5
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312236B2

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