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

HRID 468661Notes

Reaction equation

HRID 468661 reaction equation
[F:1][C:2]1[C:3]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]3[S:35][CH:36]=[CH:37][N:38]=3)[CH:28]=2)=[CH:4][C:5](=[O:26])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][O:14]C2CCCCO2)=[O:12])[CH:7]=1.FC1C(C2C=CC(N3N=CC=N3)=CC=2)=CC(=O)N(CC[C@@](C)(S(C)(=O)=O)C(NO)=O)C=1>>[F:1][C:2]1[C:3]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([O:33][C:34]3[S:35][CH:36]=[CH:37][N:38]=3)[CH:28]=2)=[CH:4][C:5](=[O:26])[N:6]([CH2:8][CH2:9][C@@:10]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([NH:13][OH:14])=[O:12])[CH:7]=1

Participants

3

Reactant 2

HCID 60199135(2R)-4-{5-Fluoro-2-oxo-4-[4-(2H-1,2,3-triazol-2-yl)phenyl]pyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideHCID 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)butanamide

Product 1

HCID 86670665(2R)-4-{5-fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 69.4%

Procedure

The title compound (66.8 mg, 68.4%) was prepared as a 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)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (115 mg, 0.20 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}-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide, Example 26, Step E. MS (LCMS) m/z 482.2 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (s, 3H) 2.09-2.23 (m, 1H) 3.11 (s, 3H) 3.70-3.87 (m, 1H) 3.97-4.14 (m, 1H) 6.58 (d, J=7.61 Hz, 1H) 7.25-7.35 (m, 2H) 7.45-7.67 (m, 4H) 8.06 (d, J=6.44 Hz, 1H) 9.23 (s, 1H) 11.08 (s, 1H).

Sources & evidence

ORD record
ord-c7f142b573d04af4ad50dba9ce851ab2
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

Loading…