HCID 44242274, compound → HCID 44242339, compound

HRID 1446060Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:29]2[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]2=[O:39])[CH:5]=[CH:6][C:7]=1[C:8]1[C:9](OC)=N[C:11]([O:14][C@@H:15]2[CH2:20][O:19][C:18]3=[N:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][N:17]3[CH2:16]2)=[N:12][CH:13]=1.Br[C:41]1C=C(C)C(O[C@@H]2COC3=NC([N+]([O-])=O)=CN3C2)=N[CH:46]=1>>[F:1][C:2]1[CH:3]=[C:4]([N:29]2[CH2:33][C@H:32]([CH2:34][NH:35][C:36](=[O:38])[CH3:37])[O:31][C:30]2=[O:39])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[N:12][C:11]([O:14][C@@H:15]2[CH2:20][O:19][C:18]3=[N:21][C:22]([N+:24]([O-:26])=[O:25])=[CH:23][N:17]3[CH2:16]2)=[C:41]([CH3:46])[CH:9]=1

Participants

Reactant 2

HCID 44242274HCID 44242274, compound

HCID 68547605HCID 68547605, compound

Product 1

HCID 44242339HCID 44242339, compound

Procedure

N-(3-{3-Fluoro-4-[4-methoxy-2-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6(S)-yloxy)-pyrimidin-5-yl]-phenyl}-2-oxo-oxazolidin-5(S)-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-3-methyl-pyridin-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 527.3 (M+H+); 1H NMR (400 MHz, CDCl3) δ 7.95 (s, 1H), 7.56 (s, 1H), 7.49 (dd, J=12.8, 2.0 Hz, 1H), 7.38 (s, 1H), 7.32 (t, J=8.4 Hz, 1H), 7.24-7.21 (m, 1H), 5.89 (t, J=6.0 Hz, 1H), 5.73 (s, 1H), 4.78-4.75 (m, 2H), 4.48 (d, J=12.8 Hz, 1H), 4.36 (d, J=2.4 Hz, 2H), 3.76 (dd, J=9.2, 6.8 Hz, 1H), 3.66-3.59 (m, 2H), 2.10 (s, 3H), 1.97 (s, 3H).

Sources & evidence

ORD record: ord-59dad01513034c25b60cceaeb1bdb418
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666864B2

Reaction notes

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