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

HRID 1043553Notes

Reaction equation

HRID 1043553 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH:9]([NH2:13])[CH2:8][O:7]2)([O-:3])=[O:2].[F:14][C:15]([F:39])([F:38])[O:16][C:17]1[CH:37]=[CH:36][C:20]([O:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33](Cl)=[O:34])[CH2:24][CH2:23]2)=[CH:19][CH:18]=1>>[F:39][C:15]([F:14])([F:38])[O:16][C:17]1[CH:18]=[CH:19][C:20]([O:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][O:30][CH2:31][CH2:32][C:33]([NH:13][C@@H:9]3[CH2:8][O:7][C:6]4=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][N:11]4[CH2:10]3)=[O:34])[CH2:24][CH2:23]2)=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 598406212-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-amineHCID 866859053-(2-(4-(4-(Trifluoromethoxy)phenoxy)piperidin-1-yl)ethoxy)propionyl chloride

Product 1

HCID 715778003-(2-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)ethoxy)-N-((S)-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl) propanamideYield 38%

Procedure

Similar to the manipulation of example 22, with (S)-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6-amine (110 mg, 0.6 mmol) and 3-(2-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)ethoxy) propionyl chloride (296 mg, 0.72 mmol) as crude materials, title compound as 124 mg yellow powder was generated and yield was 38%.

Sources & evidence

ORD record
ord-9bb54523447e47d2b61e2cc3e186ee52
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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