Dimethylformamide → HCID 57259326, compound

HRID 49828Notes

Reaction equation

HRID 49828 reaction equation
C(ON=[C:6]([C:15]1[CH:16]=[C:17]([N:21]2[C:25]3[CH:26]=[CH:27][C:28]([C:30](=[O:32])[CH3:31])=[CH:29][C:24]=3[N:23]=[CH:22]2)[CH:18]=[CH:19][CH:20]=1)[O:7]C1CCN(C)CC1)(C)C.C[O:34][C:35](OC)(C)[CH3:36].[CH3:40][N:41]([CH:43]=O)[CH3:42]>>[CH3:42][N:41]([CH3:40])[CH:43]=[CH:31][C:30]([C:28]1[CH:27]=[CH:26][C:25]2[N:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([C:6]([O:34][CH2:35][CH3:36])=[O:7])[CH:16]=3)[CH:22]=[N:23][C:24]=2[CH:29]=1)=[O:32]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 64952,2-DimethoxypropaneHCID 874575735-Acetyl-1-(3-(1-methyl-4-piperidyloxycarbonyl)phenyl)benzimidazole O-isopropyl oxime

Product 1

HCID 57259326HCID 57259326, compoundYield 62%

Conditions

Temperature
120 °C

Procedure

To a suspension of 5-acetyl-1-(3-(methoxycarbonyl)phenyl)benzimidazole (prepared in analogy with Example 26) (0.6 g, 2.04 mmol) in anhydrous DMF (5 ml) was added dimethylformaldehyde dimethylacetal (0.43 ml, 3.24 mmol) and the mixture was heated to 120° C. under a stream of nitrogen overnight. The cooled mixture was poured into ice-water (25 ml) and the precipitate was filtered off and purified by column-chromatography on silica gel using a mixture of ethyl acetate and methanol (9:1 v/v) as the eluent to yield 5-(3-dimethylaminopropenoyl)-1-(3-(ethoxycarbonyl)phenyl)-benzimidazole (0.44 g, 62%).

Workup

  1. filtrationthe precipitate was filtered off
  2. custompurified by column-chromatography on silica gel using
  3. additiona mixture of ethyl acetate and methanol (9:1 v/v) as the eluent

Sources & evidence

ORD record
ord-cd6ec71d85d344e6974aaba21559bab7
Source dataset
uspto-grants-2004_03
Patent number
US06710044B2

Reaction notes

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