1-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one → 4-[5-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]-dec-8-ylmethyl)imidazol-1-ylmethyl]benzonitrile

HRID 565596Notes

Reaction equation

HRID 565596 reaction equation
[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:19]([C:21]1[CH:34]=[CH:33][C:24]([CH2:25][N:26]2[C:30]([CH2:31]Cl)=[CH:29][N:28]=[CH:27]2)=[CH:23][CH:22]=1)#[N:20].C(N(C(C)C)CC)(C)C>C(#N)C>[O:17]=[C:10]1[C:11]2([CH2:12][CH2:13][N:14]([CH2:31][C:30]3[N:26]([CH2:25][C:24]4[CH:33]=[CH:34][C:21]([C:19]#[N:20])=[CH:22][CH:23]=4)[CH:27]=[N:28][CH:29]=3)[CH2:15][CH2:16]2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][NH:9]1

Participants

5

Reactant 3

HCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 81531DiisopropylethylamineHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochloride

Product 1

HCID 98453804-[5-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]-dec-8-ylmethyl)imidazol-1-ylmethyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (230 mg, 1 mmol), 1-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt (265 mg, 1 mmol), and diisopropylethylamine (0.52 mL, 3 mmol) in anhydrous acetonitrile (5 mL) was stirred at room temp. for 2 days. 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. concentrationThe resulting mixture was concentrated under vacuum
  2. customThe appropriate fractions were collected
  3. concentrationconcentrated
  4. customThe residue was triturated with diethyl ether
  5. customthe white solid precipitated
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-5f90ff147f054e1f99a6d5718902709b
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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