4-(4-(Trifluoromethoxy)phenyl)piperidine → N-((S)-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-2-(4-(4-(trifluoromethoxy)phenyl)piperidin-1-yl)acetamide

HRID 1043548Notes

Reaction equation

HRID 1043548 reaction equation
Cl[CH2:2][C:3]([NH:5][C@@H:6]1[CH2:11][O:10][C:9]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:8]2[CH2:7]1)=[O:4].[F:18][C:19]([F:34])([F:33])[O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1>>[N+:15]([C:13]1[N:12]=[C:9]2[N:8]([CH:14]=1)[CH2:7][C@H:6]([NH:5][C:3](=[O:4])[CH2:2][N:30]1[CH2:31][CH2:32][CH:27]([C:24]3[CH:25]=[CH:26][C:21]([O:20][C:19]([F:18])([F:33])[F:34])=[CH:22][CH:23]=3)[CH2:28][CH2:29]1)[CH2:11][O:10]2)([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 212682884-(4-(Trifluoromethoxy)phenyl)piperidineHCID 68207026(S)-2-chloro-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamide

Product 1

HCID 86685916N-((S)-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-2-(4-(4-(trifluoromethoxy)phenyl)piperidin-1-yl)acetamideYield 60%

Procedure

Similar to the manipulation of example 1, with (S)-2-chloro-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamide (130 mg, 0.50 mmol) and 4-(4-(trifluoromethoxy)phenyl)piperidine (245 mg, 1.0 mmol) as crude materials, 140 mg title compound was generated and yield was 60%.

Sources & evidence

ORD record
ord-f18cf34924e642afa5d9e661ae1aefe9
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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