Triethylamine → 6-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3,4-dihydroquinolin-2(1H)-one

HRID 1767711Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767711
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.CC(O)(C)C.ClCCCl.[NH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]2.C(N(CC)CC)C>[Cl-].[Cl-].[Zn+2].ClCCCl>[Cl:8][C:6]1[C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=[C:2]([NH:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]3)[N:7]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 49127596-amino-3,4-dihydroquinolin-2(1H)-oneHCID 21868497Tert-butyl alcohol 1,2-dichloroethane

Produkt 1

HCID 211146356-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3,4-dihydroquinolin-2(1H)-oneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 2,4-Dichloro-5-trifluoromethyl-pyrimidine (963 mg, 4.43 mmol) in 30 mL of 50/50 mixture of t-BuOH/DCE was added a solution of ZnCl2 (1M in THF;4.43 mL). After one hour 6-Amino-3,4-dihydro-1H-quinolin-2-one (480 mg;2.95 mmol) was added followed by the dropwise addition of triethylamine (0.617 ml, 4.43 mmol) in 2 mL t-BUOH/DCE. Following removal of the solvent under reduced pressure, the crude reaction was triturated from methanol and the product filtered off as a yellow solid 723 mg (72% yield). 1H NMR (DMSO-d6, 400 MHz) δ 2.39 (t, J=12 Hz; 2H), 2.80 (t, J=8 Hz; 2H), 6.78 (d, J=8 Hz; 1H), 7.35 (d, J=8 Hz; 1H), 7.40 (br s, 1H), 8.70 (s, 1H), 10.02 (s, 1H), 10.48 (s, 1H). HPLC ret. time: 6.074 (96% purity), LRMS (M+) 343.2/345.2.

Aufarbeitung

  1. customremoval of the solvent under reduced pressure
  2. customthe crude reaction
  3. customwas triturated from methanol

Quellen und Nachweise

ORD-Eintrag
ord-8c956111d587466f9d4d62755db0d0ac
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235562B2

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