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

HRID 1043552Notes

Reaction equation

HRID 1043552 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:34])([F:33])[O:16][C:17]1[CH:32]=[CH:31][C:20]([O:21][CH:22]2[CH2:25][N:24]([CH2:26][CH2:27][C:28](Cl)=[O:29])[CH2:23]2)=[CH:19][CH:18]=1>>[F:34][C:15]([F:14])([F:33])[O:16][C:17]1[CH:32]=[CH:31][C:20]([O:21][CH:22]2[CH2:25][N:24]([CH2:26][CH2:27][C:28]([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:29])[CH2:23]2)=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 598406212-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-amineHCID 866859033-(3-(4-(Trifluoromethoxy)phenoxy)azetidin-1-yl)propionyl chloride

Product 1

HCID 715777993-(3-(4-(trifluoromethoxy)phenoxy)azetidin-1-yl)-N-((S)-6,7-dihydro-2-nitro-5H-imidazo[2,1-b][1,3]oxazin-6-yl) propanamideYield 32%

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-(3-(4-(trifluoromethoxy)phenoxy)azetidin-1-yl) propionyl chloride (242 mg, 0.72 mmol) as crude materials, title compound as 91 mg yellow powder was generated and yield was 32%.

Sources & evidence

ORD record
ord-64b5d481a27e4f89ab6d9da92829231e
Source dataset
uspto-grants-2013_10
Patent number
US08563547B2

Reaction notes

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