Water → HCID 21254654, compound

HRID 2287601Notes

Reaction equation

HRID 2287601 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([Cl:41])=[C:23]([C:37]([Cl:40])=[CH:38][CH:39]=2)[CH2:24][O:25][C:26]2[C:34]3[N:33]=[C:32]([O:35][CH3:36])[NH:31][C:30]=3[CH:29]=[CH:28][CH:27]=2)[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl.[CH3:43][N:44]([CH3:48])[CH2:45][CH2:46]Cl.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([Cl:41])=[C:23]([C:37]([Cl:40])=[CH:38][CH:39]=2)[CH2:24][O:25][C:26]2[C:34]3[N:33]=[C:32]([O:35][CH3:36])[N:31]([CH2:46][CH2:45][N:44]([CH3:48])[CH3:43])[C:30]=3[CH:29]=[CH:28][CH:27]=2)[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][CH2:16][C:17]([N:19]([C:21]2[C:22]([Cl:41])=[C:23]([C:37]([Cl:40])=[CH:38][CH:39]=2)[CH2:24][O:25][C:26]2[C:34]3[N:33]([CH2:46][CH2:45][N:44]([CH3:48])[CH3:43])[C:32]([O:35][CH3:36])=[N:31][C:30]=3[CH:29]=[CH:28][CH:27]=2)[CH3:20])=[O:18])=[O:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 21254765HCID 21254765, compound

Product 2

HCID 21254654HCID 21254654, compoundHCID 21254694HCID 21254694, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1H-benzimidazole (100 mg) and 2-dimethylaminoethyl chloride hydrochloride (25.6 mg) in N,N-dimethylformamide (2 ml) was added potassium carbonate (92.5 mg) at ambient temperature, and the mixture was stirred for 28 hours at the same temperature. The reaction mixture was poured into water, and extracted with chloroform. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography to give 4-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-(2-dimethylaminoethyl)-1H-benzimidazole (11 mg) and 7-[3-[N-[(E)-3-(6-acetamidopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-(2-dimethylaminoethyl)-1H-benzimidazole (38 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-608096e5043644dcb065b4ac09270771
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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