Triethylamine → HCID 9932669, compound

HRID 1071999Notes

Reaction equation

HRID 1071999 reaction equation
[CH:1]1([CH2:7][CH2:8][CH:9]2[C:14]3[N:15]=[CH:16][NH:17][C:13]=3[CH2:12][CH2:11][NH:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:25][C:26]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:27]=1[CH2:28][N:29]=[C:30]=[O:31]>C(O)C>[CH:1]1([CH2:7][CH2:8][CH:9]2[C:14]3[N:15]=[CH:16][NH:17][C:13]=3[CH2:12][CH2:11][N:10]2[C:30]([NH:29][CH2:28][C:27]2[CH:32]=[CH:33][C:34]([Cl:36])=[CH:35][C:26]=2[Cl:25])=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46127082,4-Dichlorobenzyl isocyanateHCID 22390909HCID 22390909, compound

Product 1

HCID 9932669HCID 9932669, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-cyclohexylethyl)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine (0.47 g, 2.0 mmol, prepared as described in Example 13) in ethanol (10 mL), triethylamine (0.28 ml, 2.0 mmol) and 2,4-dichlorobenzyl isocyanate (0.41 g, 2.0 mmol) were added dropwise. The mixture was stirred overnight at room temperature and then concentrated under reduced pressure. The residue was re-evaporated with acetone and then dissolved in acetone (15 mL) and left for crystallization. The solid was isolated by filtration, washed with acetone and dried. This afforded 0.60 g (69%) of the title compound as a solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was re-evaporated with acetone
  3. dissolutiondissolved in acetone (15 mL)
  4. waitleft for crystallization
  5. customThe solid was isolated by filtration
  6. washwashed with acetone
  7. customdried

Sources & evidence

ORD record
ord-d8bde9a554e548fab311b40c3c0759de
Source dataset
uspto-grants-2005_06
Patent number
US06908926B1

Reaction notes

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