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

HRID 1043547Notes

Reaction equation

HRID 1043547 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].[CH:18]1([O:21][CH2:22][CH2:23][O:24][C:25]2[CH:37]=[CH:36][C:28]([O:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>>[CH:18]1([O:21][CH2:22][CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]([O:29][CH:30]3[CH2:35][CH2:34][N:33]([CH2:2][C:3]([NH:5][C@@H:6]4[CH2:11][O:10][C:9]5=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:8]5[CH2:7]4)=[O:4])[CH2:32][CH2:31]3)=[CH:36][CH:37]=2)[CH2:20][CH2:19]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 866859154-(4-(2-(Cyclopropoxy)ethoxy)phenoxy)piperidine

Product 1

HCID 71577724(S)-2-(4-(4-(2-(cyclopropoxy)ethoxy)phenoxy)piperidin-1-yl)-N-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)acetamideYield 39%

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-(cyclopropoxy)ethoxy)phenoxy)piperidine (277 mg, 1.0 mmol) as crude materials, 97 mg title compound was generated and yield was 39%.

Sources & evidence

ORD record
ord-36a66738a2e8402db136881ff06ea2af
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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