Methanol → HCID 10195352, Verbindung

HRID 2110001

Reaktionsgleichung

[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH:22][C:23]1[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:24]=1[CH:25]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>CS(C)=O.C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:25][C:24]4[CH:27]=[C:28]([Cl:32])[CH:29]=[C:30]([Cl:31])[C:23]=4[OH:22])[CH2:18][CH2:17]3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

After dissolving 2-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid methyl ester (20 mg, 0.055 mmol) in dimethylsulfoxide-acetic acid (10:1), 2-hydroxy-3,5-dichlorobenzaldehyde (32.0 mg, 0.166 mmol) and sodium triacetoxyborohydride (35.0 mg, 0.166 mg) were added and the mixture was stirred at 50° C. for 2 days. Methanol (1 ml) was added to the reaction mixture, and then after stirring for 1 minute, it was purified by SCX solid phase extraction (Bond Elute SCX500MG). The product was further purified by preparative HPLC to obtain 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid methyl ester. The compound was identified by LC-MS.

Aufarbeitung

additionwere added
stirringafter stirring for 1 minute
customit was purified by SCX solid phase extraction (Bond Elute SCX500MG)
customThe product was further purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-432aaa06404b40bea99d45bff01826f0
Quelldatensatz: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07517875B2

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