Methylamine → HCID 19354658, compound

HRID 377559Notes

Reaction equation

HRID 377559 reaction equation
[CH3:1][NH2:2].[F:3][C:4]([F:33])([F:32])[C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:31])[C:13]([N:16]2[C:21](=[O:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:19]([CH2:29]Br)[O:18][CH2:17]2)([CH3:15])[CH3:14])[CH:8]=[CH:9][CH:10]=1.C(OCC)(=O)C>C(O)C>[F:3][C:4]([F:33])([F:32])[C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:31])[C:13]([N:16]2[C:21](=[O:22])[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:19]([CH2:29][NH:2][CH3:1])[O:18][CH2:17]2)([CH3:15])[CH3:14])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8857Ethyl AcetateHCID 19354578HCID 19354578, compound

Product 1

HCID 19354658HCID 19354658, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Methylamine (2 ml of a 33% solution in ethanol) was added to a stirred suspension of N-(3-trifluoromethylphenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (0.5 g) in ethanol. Stirring was maintained at room temperature for 1 hour. The solution was diluted (ethyl acetate), washed (water), dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel, eluting with methanol/hexane to give N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-methylaminomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 105, 0.21 g) as an orange gum, NMR (CDCl3)δ 1.6(s,6H), 2.25(s,3H), 3.25(s,2H), 5.3(s,2H), 7.1-7.3(m,8H), 7.55(m,1H), 7.75(s,1H), 8.45(s,1H);

Workup

  1. washwashed (water)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated
  4. customThe residue was purified
  5. customby dry column chromatography on silica gel
  6. washeluting with methanol/hexane

Sources & evidence

ORD record
ord-aa26fc10e92b432d98ab6091d3c5e5ca
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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