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

HRID 1043544Notes

Reaction equation

HRID 1043544 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].[CH3:18][O:19][CH2:20][CH2:21][O:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:25][CH:24]=1>>[CH3:18][O:19][CH2:20][CH2:21][O:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH:28]2[CH2:33][CH2:32][N:31]([CH2:2][C:3]([NH:5][C@@H:6]3[CH2:11][O:10][C:9]4=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:8]4[CH2:7]3)=[O:4])[CH2:30][CH2:29]2)=[CH:25][CH:24]=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 866859114-(4-(2-Methoxyethoxy)phenoxy)piperidine

Product 1

HCID 71577644(S)-2-(4-(4-(2-methoxyethoxy)phenoxy)piperidin-1-yl)-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamideYield 56.4%

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-(2-methoxyethoxy)phenoxy)piperidine (251 mg, 1.0 mmol) as crude materials, 134 mg title compound was generated and yield was 56%.

Sources & evidence

ORD record
ord-c33334d65f5943e481a978168ba691fa
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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