(2R)-4-{5-Fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)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)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

HRID 468660Notes

Reaction equation

HRID 468660 reaction equation
[F:1][C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH:21]=2)=[CH:4][C:5](=[O:19])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:18])([S:14]([CH3:17])(=[O:16])=[O:15])[C:11]([OH:13])=O)[CH:7]=1.FC1C(C2C=CC(N3N=CC=N3)=CC=2)=CC(=O)N(CC[C@@](C)(S(C)(=O)=O)C([NH:44][O:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)=O)C=1>>[F:1][C:2]1[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH:21]=2)=[CH:4][C:5](=[O:19])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:18])([S:14]([CH3:17])(=[O:16])=[O:15])[C:11]([NH:44][O:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)=[O:13])[CH:7]=1

Participants

3

Reactant 2

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 acidHCID 86670652(2R)-4-{5-fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 86670664(2R)-4-{5-Fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamideYield 65.8%

Procedure

The title compound (115 mg, 65.8%) was prepared as an off-white solid from (2R)-4-{5-fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoic acid (144 mg, 0.31 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)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide, Example 26, Step D. MS (LCMS) m/z 566.2 (M−1).

Sources & evidence

ORD record
ord-3ec64e69f2fd4b2bbb0825278bab6453
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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