Triethylamine → HCID 178425210, Verbindung

HRID 1500987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500987
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[N:19])[C:5]([OH:7])=O.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:49][CH2:50][C:51]1[C:52]([OH:59])=[N:53][C:54]([CH3:58])=[CH:55][C:56]=1[CH3:57]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[N:19])[C:5]([NH:49][CH2:50][C:51]1[C:52]([OH:59])=[N:53][C:54]([CH3:58])=[CH:55][C:56]=1[CH3:57])=[O:7]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 613963023-Chloro-4-(2-cyanophenoxy)benzoic acidHCID 178425242HCID 178425242, Verbindung

Produkt 1

HCID 178425210HCID 178425210, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-4-(2-cyanophenoxy)benzoic acid (100 mg, 0.37 mmol) in dichloromethane (20 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (91 mg, 0.48 mmol), N-hydroxybenzotriazole (65 mg, 0.48 mmol) and triethylamine (104 mg, 0.7 mmol), stirred for 30 minutes. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (56 mg, 0.37 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was washed with water (50 mL). The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to afford 3-chloro-4-(2-cyanophenoxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (34 mg, 58%) as white solid. LRMS (M+H+) m/z: calcd 407.1. found 407; 1H-NMR (300 MHz, CD3OD) δ 11.47 (s, 1H), 8.53 (m, 1H), 8.14 (d, J=2.1 Hz, 1H), 7.90 (m, 2H), 7.68 (m, 1H), 7.29 (m, 2H), 6.93 (d, J=0.9 Hz, 1H), 5.86 (s, 1H), 4.29 (d, 2H, J=4.8 Hz), 2.17 (s, 3H), 2.11 (s, 3H).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washThe mixture was washed with water (50 mL)
  3. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-128792943ecb476099f484f77e805c44
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206128B2

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