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

HRID 1043536Notes

Reaction equation

HRID 1043536 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]1[CH:31]=[C:30]([O:32][C:33]([F:36])([F:35])[F:34])[CH:29]=[CH:28][C:20]=1[O:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>>[F:18][C:19]1[CH:31]=[C:30]([O:32][C:33]([F:34])([F:36])[F:35])[CH:29]=[CH:28][C:20]=1[O:21][CH:22]1[CH2:23][CH2:24][N:25]([CH2:2][C:3]([NH:5][C@@H:6]2[CH2:11][O:10][C:9]3=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:8]3[CH2:7]2)=[O:4])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 68207026(S)-2-chloro-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamideHCID 68207055HCID 68207055, compound

Product 1

HCID 715775522-(4-(2-fluoro-4-(trifluoromethoxy)phenoxy)piperidin-1-yl)-N-((S)-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamideYield 51%

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-(2-fluoro-4-(trifluoromethoxy)phenoxy)piperidine (279 mg, 1.0 mmol) as crude materials, 128 mg title compound was generated and yield was 51%.

Sources & evidence

ORD record
ord-4b9fce7f3bc94a08afaec49f071f5a1d
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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