Potassium Carbonate → 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methoxy-1-methyl-1H-benzimidazol-4-yloxymethyl)phenyl]pyrrole

HRID 613624Notes

Reaction equation

HRID 613624 reaction equation
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([O:11][CH3:12])[N:7](C)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14]([NH:17][C:18]1[N:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([NH:28][CH2:29][C:30]2[N:31]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([CH2:42]OS(C)(=O)=O)[C:36]=3[Cl:48])[CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].[C:49](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:14]([NH:17][C:18]1[N:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([NH:28][CH2:29][C:30]2[N:31]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([CH:42]([O:1][C:2]4[C:10]5[N:9]=[C:8]([O:11][CH3:12])[NH:7][C:6]=5[CH:5]=[CH:4][CH:3]=4)[CH3:49])[C:36]=3[Cl:48])[CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 106548994-hydroxy-2-methoxy-1-methyl-1H-benzimidazoleHCID 183217612-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(methanesulfonyloxymethyl)phenyl]pyrrole

Product 1

HCID 183218612-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methoxy-1-methyl-1H-benzimidazol-4-yloxymethyl)phenyl]pyrroleYield 23.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxy-2-methoxy-1-methyl-1H-benzimidazole (47.4 mg), 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(methanesulfonyloxymethyl)phenyl]pyrrole (143 mg) and potassium carbonate (110 mg) in N,N-dimethylformamide (4 ml) was stirred at ambient temperature for 3.5 days. The mixture was partitioned between chloroform and water. The separated organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=9:1, V/V) to give 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methoxy-1-methyl-1H-benzimidazol-4-yloxymethyl)phenyl]pyrrole (39 mg) as colorless crystals.

Workup

  1. customThe mixture was partitioned between chloroform and water
  2. dry with materialThe separated organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=9:1, V/V)

Sources & evidence

ORD record
ord-f1f8360dc65d4d72be531b5c50ccd4bc
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

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