Ethyl formate → HCID 86759018, compound

HRID 1370132Notes

Reaction equation

HRID 1370132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[N:8]([C@H:17]2[CH2:21][CH2:20][NH:19][CH2:18]2)[C:7]1=[O:22].[CH:28](OCC)=[O:29]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[N:8]([C@H:17]2[CH2:21][CH2:20][N:19]([CH:28]=[O:29])[CH2:18]2)[C:7]1=[O:22]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 70015775HCID 70015775, compound

Product 1

HCID 86759018HCID 86759018, compound

Procedure

A solution of 3-(3-chloro-4-methoxybenzyl)-5-cyano-1-[(S)-pyrrolidin-3-yl]-2,3-dihydro-1H-benzimidazol-2-one (80 mg) in ethyl formate (2 mL) was heated under reflux for 10 hours. After evaporation of the solvent, the residue was subjected to a preparative thin-layer chromatography eluting with a mixture of chloroform and methanol (15:1) to give 3-(3-chloro-4-methoxybenzyl)-5-cyano-1-[(S)-1-formylpyrrolidin-3-yl]-2,3-dihydro-1H-benzimidazol-2-one (52 mg) as amorphous powders.

Workup

  1. temperatureunder reflux for 10 hours
  2. customAfter evaporation of the solvent
  3. washeluting with a mixture of chloroform and methanol (15:1)

Sources & evidence

ORD record
ord-14b3ac55f4f6419bae9d0ad12b7c456a
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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