Methanol → HCID 10238744, Verbindung

HRID 2110005

Reaktionsgleichung

[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:16]2[N:15]=[C:14]([NH:17][CH2:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:7].[OH:25][C:26]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:27]=1[CH:28]=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][CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:16]2[N:15]=[C:14]([NH:17][CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([CH2:28][C:27]4[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:26]=4[OH:25])[CH2:23][CH2:24]3)[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:7]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

After dissolving 2-[(piperidin-4-ylmethyl)-amino]-1H-benzimidazole-4-carboxylic acid (2-methoxy-ethyl)-amide (20 mg, 0.049 mmol) in dimethylsulfoxide-acetic acid (10:1, 0.50 ml), 2-hydroxy-5-chlorobenzaldehyde (23 mg, 0.15 mmol) and sodium triacetoxyborohydride (31 mg, 0.15 mg) were added and the mixture was stirred at 50° C. for 2 days. Methanol (1 ml) was added to the reaction mixture, and after stirring for 1 minute, the mixture was purified by SCX solid phase extraction (Bond Elute SCX500MG). The product was further purified by preparative HPLC to obtain 2-{[1-(5-chloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid (2-methoxy-ethyl)-amide. The compound was identified by LC-MS.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-bcd1af0e36d94e9ab600e18a4845f604
Quelldatensatz: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07517875B2

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