Water → HCID 18536471, compound

HRID 412625Notes

Reaction equation

HRID 412625 reaction equation
[CH:1]1([NH:7][C:8]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]#[N:21])=[CH:19][C:14]=3[N:13]=[C:12]2[CH:22]([NH:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)C2C=CN=CC=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])C.[C:43](Cl)(=[O:49])[C:44]([O:46][CH2:47][CH3:48])=[O:45].O.[CH:52](Cl)(Cl)Cl>>[CH:1]1([NH:7][C:8]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]#[N:21])=[CH:19][C:14]=3[N:13]=[C:12]2[CH2:22][N:29]([CH:30]2[CH2:35][CH2:34][N:33]([C:52]3[CH:40]=[CH:39][N:38]=[CH:41][CH:42]=3)[CH2:32][CH2:31]2)[C:43]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:49])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 962WaterHCID 6212ChloroformHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 69698843HCID 69698843, compound

Product 1

HCID 18536471HCID 18536471, compound

Procedure

To a solution of 1-(cyclohexylcarbamoylmethyl)-5-cyano-2-[1-(pyridin-4-yl)piperidin-4-ylaminomethyl]benzimidazole (203 mg) and triethylamine (0.18 ml) in chloroform (5 ml) was added ethyl chlorooxalate (0.119 ml), and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, water was added, and the mixture was extracted with chloroform and washed with aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5, 1% aqueous ammonia) and dried under reduced pressure to give the title compound (205 mg).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with chloroform
  3. washwashed with aqueous sodium hydrogencarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5, 1% aqueous ammonia)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd771b9bf60d42ad931c7bf3f916ff66
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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