Diisopropylethylamine → L 697639

HRID 1032999Notes

Reaction equation

HRID 1032999 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 697639Yield 44%

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 atmosphere of nitrogen for 12 hours. The resultant mixture was concentrated under reduced pressure (15 torr). The residue was then subjected to column chromatography on silica gel (100 g, elution with 4% methanol in chloroform). Collection and concentration of appropriate fractions provided 0.2 g (44%) of the benzoxazolylmethylaminopyridone. Anal. Calcd. for C18H21N3O2 : C, 69.43; H, 6.80; N, 13.49. Found: C, 69.32; H, 6.66; N, 13.47.

Workup

  1. temperaturewas refluxed under an atmosphere 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-ac29b078ac604fea8c0158678fe9ac69
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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