Ammonium Chloride → (R)-5-(5-Bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

HRID 1929482Notes

Reaction equation

HRID 1929482 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C@@:8]2([CH3:15])[NH:13][C:12](=O)[CH2:11][O:10][CH2:9]2)[CH:7]=1.[Cl-].[NH4+:18]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C@:8]2([CH3:15])[CH2:9][O:10][CH2:11][C:12]([NH2:18])=[N:13]2)[CH:7]=1

Participants

3

Reactant 2

HCID 25517Ammonium ChlorideHCID 58155287(R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one

Product 1

HCID 58155238(R)-5-(5-Bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

Procedure

In analogy to step a) in the synthesis of Building block I, the treatment of (R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one followed by the nucleophilic substitution with ammonium chloride yielded the title compound; its hydrochloride was obtained as a white solid (74% of theory). Mass (calculated) C11H12BrFN2O [287.13]; (found) [M+H]+=287, [M+2-H]+=289.

Workup

  1. customIn analogy to step a) in the synthesis of Building block I

Sources & evidence

ORD record
ord-069df985cd81414aa97380d0e1df8f15
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

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