(2E)-3-(4-Chlorophenyl)acryloyl chloride → (2E)-3-(4-chlorophenyl)-N-(2-piperidin-1-ylquinolin-6-yl)prop-2-enamide hydrochloride

HRID 6798

Reaktionsgleichung

Reaktionsgleichung von HRID 6798
[N:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27](Cl)=[O:28])=[CH:21][CH:20]=1.N1C2C(=CC(N)=CC=2)C=CC=1N>CC(O)=O.CCOCC>[ClH:18].[Cl:18][C:19]1[CH:20]=[CH:21][C:22](/[CH:25]=[CH:26]/[C:27]([NH:17][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:16]=[CH:15]3)=[O:28])=[CH:23][CH:24]=1

Komponenten

6

Edukt 3

HCID 11252649(2E)-3-(4-Chlorophenyl)acryloyl chlorideHCID 22018948Quinoline-2,6-diamineHCID 220189742-Piperidin-1-ylquinolin-6-amine

Produkt 1

HCID 22018962(2E)-3-(4-chlorophenyl)-N-(2-piperidin-1-ylquinolin-6-yl)prop-2-enamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of the product of Step D (91 mg, 0.4 mmol) in 2 mL HOAc was added the product of Step E (64 mg, 0.32 mmol). The resulting mixture was stirred at r.t. for 3 h then diluted with 3 mL ether. The resulting mixture was filtered and the resulting solids were washed with ether. The solids were dried under vacuum to afford the product, MS: m/z 392 (MH+), as an off-white solid. Using the appropriate starting materials and following procedures similar to those described above for Example 1, the following compounds were prepared from the corresponding quinoline-2,6-diamine intermediates:

Aufarbeitung

  1. filtrationThe resulting mixture was filtered
  2. washthe resulting solids were washed with ether
  3. customThe solids were dried under vacuum
  4. customto afford the product, MS

Quellen und Nachweise

ORD-Eintrag
ord-7ea16d5540f64108a374fefb1059f324
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084156B2

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