Diisopropylethylamine → Methyl 4-({[(2-chloro-5-{[(3-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}methyl)benzoate

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Reaktionsgleichung

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.CN(C)CCCN=C=NCC.Cl.[NH2:33][CH2:34][C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1.C(N(C(C)C)C(C)C)C>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)=[CH:7][C:3]=1[C:4]([NH:33][CH2:34][C:35]1[CH:36]=[CH:37][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:43][CH:44]=1)=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A solution of 2-chloro-5-{[(3-chlorophenyl)methyl]oxy}benzoic acid (250 mg, 0.84 mmol) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (250 mg, 1.3 mmol) in DCM (3 ml) was stirred at room temperature for 30 min. A solution of methyl 4-(aminomethyl)benzoate hydrochloride (262 mg, 1.3 mmol) in DCM (2 ml) was added followed by N-ethyl-N-(1-methylethyl)-2-propanamine (220 ul, 1.3 mmol). The mixture was heated at 40° C. overnight. The mixture was then diluted with methanol and purified by SCX cartridge eluting with methanol. The fractions were combined and evaporated to give the title compound as a white solid. MS (ES+) m/z 444 [M+H]− (C23H1935Cl2NO4). 1H-NMR (400 MHz, d6-DMSO) δ 3.85 (3H, s), 4.51 (2H, d, J 4), 5.17 (2H, s), 7.12 (2H, d, J 8), 7.42-7.49 (7H, m), 7.95 (2H, d, J 8), 9.06 (1H, s).

Aufarbeitung

custompurified by SCX cartridge
washeluting with methanol
customevaporated

Quellen und Nachweise

ORD-Eintrag: ord-f93fea5402cc47d38eba2f94e6c4389b
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08293798B2

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