Diisopropylethylamine → 1-[3-(4-Cyanobenzyl)-3H-imidazol-4-ylmethyl]-4-(3-methylbenzyl)isonipecotamide

HRID 1068460Notes

Reaction equation

HRID 1068460 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][C:7]1([C:13]([NH2:15])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]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(#N)C>[C:20]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][N:27]2[C:31]([CH2:32][N:10]3[CH2:9][CH2:8][C:7]([CH2:6][C:5]4[CH:16]=[CH:17][CH:18]=[C:3]([CH3:2])[CH:4]=4)([C:13]([NH2:15])=[O:14])[CH2:12][CH2:11]3)=[CH:30][N:29]=[CH:28]2)=[CH:34][CH:35]=1)#[N:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochlorideHCID 211933114-(3-Methylbenzyl)isonipecotamide hydrochloride salt

Product 1

HCID 211933571-[3-(4-Cyanobenzyl)-3H-imidazol-4-ylmethyl]-4-(3-methylbenzyl)isonipecotamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(3-methylbenzyl)isonipecotamide hydrochloride salt (134 mg, 0.5 mmol), 1-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt (134 mg, 0.5 mmol; Example 52, Step D), and diisopropylethylamine (440 mL, 2.5 mmol) in anhydrous acetonitrile (5 mL) was heated under reflux overnight. The resultant mixture was concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in chloroform saturated with ammonia gas. After collection and concentration of appropriate fractions, the residue was triturated with anhydrous diethyl ether. The white solid precipitated was filtered to provide the title compound.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe resultant mixture was concentrated under vacuum
  3. customAfter collection and concentration of appropriate fractions
  4. customthe residue was triturated with anhydrous diethyl ether
  5. customThe white solid precipitated
  6. filtrationwas filtered

Sources & evidence

ORD record
ord-c067d4369782411993f4f244dbd59c4f
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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