Diisopropylethylamine → L 697639

HRID 1681111Notes

Reaction equation

HRID 1681111 reaction equation
[NH2:1][C:2]1[C:3](=[O:11])[NH:4][C:5]([CH3:10])=[C:6]([CH2:8][CH3:9])[CH:7]=1.Cl[CH2:13][C:14]1[O:15][C:16]2[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([CH3:24])[C:17]=2[N:18]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:24][C:19]1[C:17]2[N:18]=[C:14]([CH2:13][NH:1][C:2]3[C:3](=[O:11])[NH:4][C:5]([CH3:10])=[C:6]([CH2:8][CH3:9])[CH:7]=3)[O:15][C:16]=2[C:22]([CH3:23])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4810223-Amino-5-ethyl-6-methyl-1H-pyridin-2-oneHCID 100355622-Chloromethyl-4,7-dimethylbenzoxazole

Product 1

HCID 60832L 697639

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-amino-5-ethyl-6-methyl-2-(1H)-pyridinone (0.23 g, 1.5 mmol),2-chloromethyl-4,7-dimethylbenzoxazole (0.29 g, 1.5 mmol, diisopropylethylamine (0.39 g, 3 mmol) in acetonitrile (50 mL) was refluxed under an atomosphere of nitrogen for 12 hours. The resultant mixture was concentrated under reduced pressure (15 torr). The residue wasthen subjected to column chromatography on silica gel (100 g, elution with 4% methanol in chloroform). Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. temperaturewas refluxed under an atomosphere of nitrogen for 12 hours
  2. concentrationThe resultant mixture was concentrated under reduced pressure (15 torr)
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-7cc5edfc40ad4e78bdb223095a806485
Source dataset
uspto-grants-1992_12
Patent number
US05169769

Reaction notes

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