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

HRID 1043541Notes

Reaction equation

HRID 1043541 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:35])([F:34])[O:20][C:21]1[CH:33]=[CH:32][C:24]([O:25][CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]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:29]1[CH2:30][CH2:31][CH:26]([O:25][C:24]3[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:34])[F:35])=[CH:33][CH:32]=3)[CH2:27][CH2:28]1)[CH2:11][O:10]2)([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 161154394-[4-(Trifluoromethoxy)phenoxy]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 71577551(S)-N-(6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-2-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)acetamideYield 56%

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)phenoxy)piperidine (275 mg, 1.0 mmol) as crude materials, title compound as 140 mg yellow powder was generated and yield was 56%.

Sources & evidence

ORD record
ord-28b9b4e539cb4aa8a833c8512ec250d5
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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