6-Phenylnicotinic acid → HCID 57682707, Verbindung

HRID 494213

Reaktionsgleichung

Reaktionsgleichung von HRID 494213
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2[C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.[C:18]1([C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:18]1([C:24]2[CH:32]=[CH:31][C:27]([C:28]([NH:1][C:2]3[CH:11]=[C:10]4[C:5]([CH2:6][CH2:7][CH2:8][N:9]4[C:12](=[O:17])[C:13]([F:16])([F:14])[F:15])=[CH:4][CH:3]=3)=[O:29])=[CH:26][N:25]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 1201186-Phenylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 82048422HCID 82048422, Verbindung

Produkt 1

HCID 57682707HCID 57682707, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 7-amino-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D5) (122 mg, 0.5 mmol) in DCM (2 ml) was added 6-phenylnicotinic acid (D48) (119 mg, 0.6 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (111 mg, 0.6 mmol) and 4-dimethylaminopyridine (7 mg, 0.06 mmol) and the reaction stirred at ambient temperature for until complete by tlc. The mixture was then washed with 2M sodium hydroxide solution (1 ml), dried over magnesium sufate and concentrated in vacuo to give the crude product which was purified by silica SPE chromatography. Elution with 20% EtOAc/60-80° C. petroleum ether gave an off-white solid which was recrystallised from EtOAc/60-80° C. petroleum ether giving the title compound as a white solid. 1H NMR (250 MHz, CDCl3) δ (ppm): 9.10 (d, 1H), 8.20 (m, 2H), 8.04 (m, 2H), 7.86 (br, 1H), 7.82 (dd, 1H), 7.72 (br, 1H), 7.50 (m, 3H), 7.19 (1H, d), 3.84 (m, 2H), 2.84 (m, 2H), 2.06 (m, 2H).

Aufarbeitung

  1. washThe mixture was then washed with 2M sodium hydroxide solution (1 ml)
  2. dry with materialdried over magnesium sufate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5b05f69c153d40d2a6b6b2d2794a6ba8
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538121B2

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