5-Amino-2-hydroxybenzimidazole → 2-Oxo-N-(2-oxo-2,3-dihydro-1H-benzimidazol-6-yl)-2-(4-p-tolyloxy-piperidin-1-yl)-acetamide

HRID 2114992

Reaction equation

HRID 2114992 reaction equation
[O:1]=[C:2]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[C:3]([OH:5])=O.[NH2:20][C:21]1[CH:30]=[CH:29][C:24]2[NH:25][C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1>>[O:1]=[C:2]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)[C:3]([NH:20][C:21]1[CH:30]=[CH:29][C:24]2[NH:25][C:26](=[O:28])[NH:27][C:23]=2[CH:22]=1)=[O:5]

Participants

3

Reactant 2

HCID 667655-Amino-2-hydroxybenzimidazoleHCID 69100252Oxo-(4-p-tolyloxy-piperidin-1-yl)-acetic acid

Product 1

HCID 102006502-Oxo-N-(2-oxo-2,3-dihydro-1H-benzimidazol-6-yl)-2-(4-p-tolyloxy-piperidin-1-yl)-acetamide

Procedure

The title compound is prepared from oxo-(4-p-tolyloxy-piperidin-1-yl)-acetic acid (Example 26b) and 5-amino-1,3-dihydro-benzimidazol-2-one according to the method described in Example 2. The filtered crystals are purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and toluene:methanol=4:1 as eluent. Melting Point: 294° C. (isopropanol)

Workup

  1. customThe filtered crystals are purified by column chromatography

Sources & evidence

ORD record
ord-51dff2f588f14f02843a66f108ba7efb
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Linked notes

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