(2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acid → (2R)-4-{5-Fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acid

HRID 468659Notes

Reaction equation

HRID 468659 reaction equation
[F:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]3[S:30][CH:31]=[CH:32][N:33]=3)[CH:23]=2)=[CH:4][C:5](=[O:21])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:20])([S:16]([CH3:19])(=[O:18])=[O:17])[C:11]([O:13]CC)=[O:12])[CH:7]=1.FC1C(C2C=CC(N3N=CC=N3)=CC=2)=CC(=O)N(CC[C@@](C)(S(C)(=O)=O)C(O)=O)C=1>>[F:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]3[S:30][CH:31]=[CH:32][N:33]=3)[CH:23]=2)=[CH:4][C:5](=[O:21])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:20])([S:16]([CH3:19])(=[O:18])=[O:17])[C:11]([OH:13])=[O:12])[CH:7]=1

Participants

3

Reactant 2

HCID 70664611(2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acidHCID 86670663Ethyl (2R)-4-{5-fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 70664620(2R)-4-{5-Fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acidYield 28.4%

Procedure

The title compound (144 mg, 28.4%) was prepared as an off-white solid from ethyl (2R)-4-{5-fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoate (538 mg, 1.09 mmol) using a procedure analogous to that described for (2R)-4-{5-fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acid, Example 26, Step C. MS (LCMS) m/z 467.1 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3H) 2.12-2.27 (m, 1H) 3.17 (s, 3H) 3.85-4.11 (m, 2H) 6.55 (d, J=7.61 Hz, 1H) 7.24-7.35 (m, 2H) 7.44-7.66 (m, 4H) 8.07 (d, J=6.44 Hz, 1H).

Sources & evidence

ORD record
ord-1f442612c570479fa272b309199f94b8
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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