1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → [bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-amine

HRID 1929483Notes

Reaction equation

HRID 1929483 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C@:8]2([CH3:15])[CH2:13][O:12][CH2:11][C:10]([NH2:14])=[N:9]2)[CH:7]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](Cl)([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1>>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([C:25]([NH:14][C:10]2[CH2:11][O:12][CH2:13][C@:8]([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[F:16])([CH3:15])[N:9]=2)([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 58155238(R)-5-(5-Bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

Product 1

HCID 66931613[bis-(4-methoxy-phenyl)-phenyl-methyl]-[(R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-amineYield 72%

Procedure

In analogy to step c) in the synthesis of Building block I, the reaction of (R)-5-(5-bromo-2-fluoro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine with 4,4′-dimethoxytriphenylmethyl chloride yielded the title compound as a white solid (72% of theory). Mass (calculated) C32H30BrFN2O3 [589.51]; (found) [M+H]+=589, [M+2-H]+=591.

Workup

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

Sources & evidence

ORD record
ord-924927d0c07641688a8469d7b28da29d
Source dataset
uspto-grants-2012_05
Patent number
US08188079B2

Reaction notes

Loading…