Ethyl isocyanate → HCID 10310912, compound

HRID 2109996Notes

Reaction equation

HRID 2109996 reaction equation
C([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([NH2:17])[C:11]=2[N:10]=[C:9]1[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.[CH2:35]([N:37]=C=O)[CH3:36].O1CCOCC1.Cl>C(#N)C>[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[Cl:33])[CH2:26][N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][NH:18][C:9]2[NH:17][C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([NH:8][C:6]([NH:37][CH2:35][CH3:36])=[O:5])[C:11]=3[N:10]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 204431481,4-Dioxane hydrochlorideHCID 69070206HCID 69070206, compound

Product 1

HCID 10310912HCID 10310912, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After dissolving 4-amino-2-{[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-amino}-benzimidazole-1-carboxylic acid tert-butyl ester (10 mg, 0.02 mmol) in acetonitrile (1 ml), ethyl isocyanate (0.08 mmol) was added and the mixture was stirred at room temperature overnight. After adding a 4N hydrogen chloride-1,4-dioxane solution (1 ml) to the reaction mixture, it was stirred at 50° C. for 1 hour and then the reaction mixture was passed through SCX (Bond Elute SCX500MG). The SCX was washed with methanol and elution was performed with a 2N ammonia-methanol solution. The solvent was distilled off under reduced pressure to obtain 1-(2-{[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazol-4-yl)-3-ethyl-urea. The compound was identified by LC-MS.

Workup

  1. additionwas added
  2. stirringwas stirred at 50° C. for 1 hour
  3. washthe reaction mixture was passed through SCX (Bond Elute SCX500MG)
  4. washThe SCX was washed with methanol and elution
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6f807dbb0e734baa821479c3ffd480e2
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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