Ammonium Chloride → 5-(5-Bromo-2-fluorophenyl)-5,6-dihydro-5-methyl-2H-1,4-oxazin-3-amine

HRID 593344Notes

Reaction equation

HRID 593344 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.F[B-](F)(F)F.C[O+](C)C.[Cl-].[NH4+:27]>>[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]([NH2:27])=[N:13]2)[CH:7]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 581552625-(5-Bromo-2-fluorophenyl)-5-methylmorpholin-3-one

Product 1

HCID 669315715-(5-Bromo-2-fluorophenyl)-5,6-dihydro-5-methyl-2H-1,4-oxazin-3-amine

Procedure

In analogy to step a) in the synthesis of building block D, the treatment of (RS)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-morpholin-3-one with trimethyloxonium tetrafluoroborate followed by the nucleophilic substitution with ammonium chloride yielded the title compound; its hydrochloride was obtained as a white solid. 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 D

Sources & evidence

ORD record
ord-82bb137a15ef4aee82d1a992f866dd19
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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