Methylamine → HCID 22013855, compound

HRID 1532738Notes

Reaction equation

HRID 1532738 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:31]=[CH:30][C:19]([CH2:20][CH:21]([C:26]([O:28]C)=O)[C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=1.[CH3:32][NH2:33]>CO.O1CCCC1>[CH3:32][NH:33][C:26]([CH:21]([CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:31][CH:30]=1)[C:22]([O:24][CH3:25])=[O:23])=[O:28]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 6918417HCID 6918417, compound

Product 1

HCID 22013855HCID 22013855, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Dimethyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]malonate (3.00 g, 7.08 mmol) synthesized according to the method described in WO95/18125 was dissolved in methanol-tetrahydrofuran (1:1, 100 ml), and 40% aqueous methylamine solution (50 ml) was added. The mixture was stirred at room temperature for 0.5 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=1:2) to give the title compound (1.50 g, yield 50%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-8800745f0b374b17a391452f3c46a893
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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