Dimethylcarbamoyl Chloride → 2-({[4-(4-dipropylaminomethylphenylcarbamoyl)-benzyl]-(1-methyl-1H-imidazol-2-ylmethyl)-amino}-methyl)-imidazol-1-carboxylic Acid Dimethylamide

HRID 348681Notes

Reaction equation

HRID 348681 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:38])[C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH2:32][C:33]3[NH:34][CH:35]=[CH:36][N:37]=3)[CH2:25][C:26]3[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=3)=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[CH3:39][N:40]([CH3:44])[C:41](Cl)=[O:42]>N1C=CC=CC=1>[CH3:39][N:40]([CH3:44])[C:41]([N:37]1[CH:36]=[CH:35][N:34]=[C:33]1[CH2:32][N:24]([CH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:16](=[O:38])[NH:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:8][N:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])=[CH:14][CH:13]=2)=[CH:22][CH:21]=1)[CH2:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1)=[O:42]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 11950262N-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzamide

Product 1

HCID 588018912-({[4-(4-dipropylaminomethylphenylcarbamoyl)-benzyl]-(1-methyl-1H-imidazol-2-ylmethyl)-amino}-methyl)-imidazol-1-carboxylic Acid DimethylamideYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound (95.0 mg) obtained in Example 49-1 was dissolved in pyridine (5.0 ml) and added with N,N-dimethylcarbamoyl chloride (20.0 mg). After the solution had been stirred at room temperature for 15 hours, pyridine was distilled off and the residue was then added with a saturated aqueous sodium bicarbonate solution and extracted with chloroform. The extract was concentrated and purified through column chromatography (chloroform/methanol), thereby obtaining the subject compound (45.4 mg) as a white solid.

Workup

  1. distillationpyridine was distilled off
  2. additionthe residue was then added with a saturated aqueous sodium bicarbonate solution
  3. extractionextracted with chloroform
  4. concentrationThe extract was concentrated
  5. custompurified through column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-d8aac73f92bb4a3892b73980bb352b1e
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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