Methyl chloroformate → 2-({[4-(4-dipropylaminomethylphenylcarbamoyl)-benzyl]-(1-methyl-1H-imidazol-2-ylmethyl)-amino}-methyl)-imidazol-1-carboxylic Acid Ethyl Ester

HRID 348665Notes

Reaction equation

HRID 348665 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].[CH2:39](N(CC)CC)C.Cl[C:47]([O:49][CH3:50])=[O:48]>C(Cl)(Cl)Cl>[CH2:50]([O:49][C:47]([N:37]1[CH:36]=[CH:35][N:34]=[C:33]1[CH2:32][N:24]([CH2:23][C:20]1[CH:21]=[CH:22][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:18][CH:19]=1)[CH2:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1)=[O:48])[CH3:39]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 11950262N-(4-dipropylaminomethylphenyl)-4-{[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl}-benzamide

Product 1

HCID 588019232-({[4-(4-dipropylaminomethylphenylcarbamoyl)-benzyl]-(1-methyl-1H-imidazol-2-ylmethyl)-amino}-methyl)-imidazol-1-carboxylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The compound (66.2 mg) obtained in Example 49-1 was dissolved in anhydrous chloroform (2.7 ml). Then, the solution was added with triethylamine (0.028 ml) and then added with methyl chloroformate (manufactured by Kanto Kagaku) (0.015 ml), followed by stirring at room temperature for 6 hours. After completion of the reaction, the solution was added with chloroform (3.0 ml), followed by washing with water and a saturated aqueous sodium bicarbonate solution. The organic layer was dried with anhydrous magnesium sulfate and the solvent was then distilled off, thereby obtaining the subject compound (65.2 mg) as a yellow viscous solid.

Workup

  1. customAfter completion of the reaction
  2. washby washing with water
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. distillationthe solvent was then distilled off

Sources & evidence

ORD record
ord-cbeb9593a86c41f0923554260fa7295d
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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