HCID 44242340, compound → HCID 44242403, compound

HRID 1446062Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:28]2[CH2:32][C@H:31]([CH2:33][NH:34][C:35](=[O:37])[CH3:36])[O:30][C:29]2=[O:38])[CH:5]=[CH:6][C:7]=1C1C(C)=NC(O[C@@H]2COC3=NC([N+]([O-])=O)=CN3C2)=CC=1.Br[C:40]1[C:41]([C:59]([F:62])([F:61])[F:60])=[N:42][C:43]([O:46][C@@H:47]2[CH2:52][O:51][C:50]3=[N:53][C:54]([N+:56]([O-:58])=[O:57])=[CH:55][N:49]3[CH2:48]2)=[N:44][CH:45]=1>>[F:1][C:2]1[CH:3]=[C:4]([N:28]2[CH2:32][C@H:31]([CH2:33][NH:34][C:35](=[O:37])[CH3:36])[O:30][C:29]2=[O:38])[CH:5]=[CH:6][C:7]=1[C:40]1[C:41]([C:59]([F:62])([F:61])[F:60])=[N:42][C:43]([O:46][C@@H:47]2[CH2:52][O:51][C:50]3=[N:53][C:54]([N+:56]([O-:58])=[O:57])=[CH:55][N:49]3[CH2:48]2)=[N:44][CH:45]=1

Participants

Reactant 2

HCID 44242340HCID 44242340, compound

HCID 68549511HCID 68549511, compound

Product 1

HCID 44242403HCID 44242403, compound

Procedure

(S,S)—N-(3-{3-Fluoro-4-[2-methyl-6-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxy)-pyridin-3-yl]-phenyl}-2-oxo-oxazolidin-5-ylmethyl)-acetamide. The title compound was prepared by following the same procedure as described in the preparation of Example 7, except 6(S)-(5-bromo-4-trifluoromethyl-pyrimidin-2-yloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine was used in place of 6(S)-(5-bromo-pyridin-2-yloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine. ESI MS m/z 582.5 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.65 (s, 1H), 7.63 (d, J=11.6 Hz, 1H), 7.48 (s, 1H), 7.32-7.25 (m, 2H), 6.02 (t, J=6.2 Hz, 1H), 5.75 (s, 1H), 4.94 (d, J=12.0 Hz, 1H), 4.83-4.82 (m, 1H), 4.60 (d, J=12.4 Hz, 1H), 4.49 (brs, 2H), 4.10 (t, J=9.8 Hz, 1H), 3.84 (t, J=7.8 Hz, 1H), 3.72-3.62 (m, 2H), 2.04 (s, 3H).

Sources & evidence

ORD record: ord-a67c444d14fc439592346e471291ebfd
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666864B2

Reaction notes

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