1-(4-Fluorophenyl)-2-methyl-2-aminopropane → 6-benzyloxy-8-{2-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylamino]-1-hydroxy-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 969468Notes

Reaction equation

HRID 969468 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:22](=[O:28])[CH:23](OCC)O)[C:12]2[O:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[NH:14][C:13]=2[CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH2:40])([CH3:39])[CH3:38])=[CH:32][CH:31]=1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:22]([OH:28])[CH2:23][NH:40][C:37]([CH3:38])([CH3:39])[CH2:36][C:33]2[CH:32]=[CH:31][C:30]([F:29])=[CH:35][CH:34]=2)[C:12]2[O:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[NH:14][C:13]=2[CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5184711-(4-Fluorophenyl)-2-methyl-2-aminopropaneHCID 210728546-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 694590206-benzyloxy-8-{2-[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylamino]-1-hydroxy-ethyl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Procedure

385 mg (1 mmol) 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one and 167 mg (1 mmol) 2-(4-fluoro-phenyl)-1,1-dimethyl-ethylamine are reacted and worked up analogously to Example 14. However, the resulting benzylether is chromatographed on a silica gel column (dichloromethane/methanol gradient).

Workup

  1. customHowever, the resulting benzylether is chromatographed on a silica gel column (dichloromethane/methanol gradient)

Sources & evidence

ORD record
ord-5ae6a2c8a6954e99a1f043c920f02b82
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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