(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-ethoxyethoxy)phenoxy)piperidin-1-yl)-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamide

HRID 1043545Notes

Reaction equation

HRID 1043545 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].[CH2:18]([O:20][CH2:21][CH2:22][O:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:26][CH:25]=1)[CH3:19]>>[CH2:18]([O:20][CH2:21][CH2:22][O:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH:29]2[CH2:34][CH2:33][N:32]([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])[CH2:31][CH2:30]2)=[CH:26][CH:25]=1)[CH3:19]

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 866859134-(4-(2-Ethoxyethoxy)phenoxy)piperidine

Product 1

HCID 86685912(S)-2-(4-(4-(2-ethoxyethoxy)phenoxy)piperidin-1-yl)-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamideYield 63%

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-ethoxyethoxy)phenoxy)piperidine (265 mg, 1.0 mmol) as crude materials, 75 mg title compound was generated and yield was 63%.

Sources & evidence

ORD record
ord-923ab11be36f40f38649cfb6507deb81
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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