Diisopropylethylamine → HCID 9889465, compound

HRID 565601Notes

Reaction equation

HRID 565601 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:11](=[O:18])[NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl.[C:20]([C:22]1[CH:35]=[CH:34][C:25]([CH2:26][N:27]2[C:31]([CH2:32]Cl)=[CH:30][N:29]=[CH:28]2)=[CH:24][CH:23]=1)#[N:21].C(N(C(C)C)CC)(C)C>C(O)C>[O:18]=[C:11]1[C:12]2([CH2:17][CH2:16][N:15]([CH2:32][C:31]3[N:27]([CH2:26][C:25]4[CH:34]=[CH:35][C:22]([C:20]#[N:21])=[CH:23][CH:24]=4)[CH:28]=[N:29][CH:30]=3)[CH2:14][CH2:13]2)[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[CH2:9][NH:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochlorideHCID 212683701-(3-Methylphenyl)-1,3,8-triazaspiro[4.5]decan-4-one

Product 1

HCID 9889465HCID 9889465, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(3-methylphenyl)-1,3,8-triazaspiro[4.5]decan-4-one (0.25 g, 0.94 mmol), 1-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt (0.23 g, 0.94 mmol), and diisopropylethylamine (0.5 mL, 2.8 mmol) in absolute ethanol (5 mL) was heated under reflux overnight. The resulting mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluting with 5% methanol in ethyl acetate. The appropriate fractions were collected and concentrated. The residue was triturated with diethyl ether, and the white solid precipitated was collected by filtration to provide the title compound.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe appropriate fractions were collected
  4. concentrationconcentrated
  5. customThe residue was triturated with diethyl ether
  6. customthe white solid precipitated
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7322606e6df94853b665e2d6e210c5ee
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

Loading…