Water → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-hydroxymethyl-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 18555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18555
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](=[O:25])[NH:15][CH:16]3[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]3)[N:10]([CH2:26][C:27](=[O:36])[NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[Li+].[BH4-].O>C1COCC1>[CH:22]([N:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:14]([C:11]2[N:10]([CH2:26][C:27](=[O:36])[NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([CH2:3][OH:2])[C:13]=3[N:12]=2)=[O:25])[CH2:17][CH2:18]1)([CH3:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 114664091-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid methyl ester

Produkt 1

HCID 670113751-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-hydroxymethyl-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

85.0 mg (0.166 mmol) 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-4-carboxylic acid methyl ester were dissolved in 3 mL abs. THF. Under argon 0.25 mL (0.497 mmol) of a 2 M LiBH4-solution in THF were added. After stirring for 1.5 h at room temperature 0.5 mL water were added and the reaction mixture was concentrated. The residue was purified by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) to give 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-4-hydroxymethyl-1H-benzoimidazole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide as a white amorphous solid. The title compound was obtained as its formiate. Yield: 20 mg MS (ES+): m/e=485, chloro pattern.

Aufarbeitung

  1. additionwere added
  2. concentrationthe reaction mixture was concentrated
  3. customThe residue was purified by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid)

Quellen und Nachweise

ORD-Eintrag
ord-23bee7d50f7d4668b4b9a00365242112
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741341B2

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