Diisopropylethylamine → HCID 15410558, compound

HRID 1068477Notes

Reaction equation

HRID 1068477 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C:6]([C:8]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7].Cl.[C:22]([C:24]1[CH:37]=[CH:36][C:27]([CH2:28][N:29]2[C:33]([CH2:34]Cl)=[CH:32][N:31]=[CH:30]2)=[CH:26][CH:25]=1)#[N:23].C(N(C(C)C)CC)(C)C>C(#N)C>[C:22]([C:24]1[CH:25]=[CH:26][C:27]([CH2:28][N:29]2[C:33]([CH2:34][N:11]3[CH2:10][CH2:9][C:8]([C:6](=[O:7])[C:5]4[CH:18]=[CH:19][CH:20]=[C:3]([CH3:2])[CH:4]=4)([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]3)=[CH:32][N:31]=[CH:30]2)=[CH:36][CH:37]=1)#[N:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochlorideHCID 21193249HCID 21193249, compound

Product 1

HCID 15410558HCID 15410558, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 4-(3-methylbenzoyl)piperidine-4-carboxylate hydrochloride salt (58 mg, 0.2 mmol), l-(4-cyanobenzyl)-5-chloromethylimidazole hydrochloride salt (52 mg, 0.19 mmol), and diisopropylethylamine (174 μL, 1 mmol) in anhydrous acetonitrile (4 mL) was heated at 60° C. overnight. The resultant mixture was concentrated under vacuum, and the residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2.5% methanol in ethyl acetate. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. customthe residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-aabc33756dcd432fb274d5a80b1cde8a
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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