HCID 178448468, compound → HCID 178448471, compound

HRID 1183945

Reaction equation

HRID 1183945 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([O:16]C3CCCCO3)[CH2:12][CH2:11]2)[CH:5]=[CH:4][C:3]=1[C:23]1[CH:28]=[CH:27][N:26]([CH2:29][CH2:30][C@@:31]([CH3:46])([S:42]([CH3:45])(=[O:44])=[O:43])[C:32]([NH:34][O:35]C2CCCCO2)=[O:33])[C:25](=[O:47])[CH:24]=1.ONC(=O)[C@](C)(S(C)(=O)=O)CCN1C=CC(C2C=CC(OC[C@H]3CC[C@@H](O)CC3)=CC=2)=CC1=O>>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][CH2:11]2)[CH:5]=[CH:4][C:3]=1[C:23]1[CH:28]=[CH:27][N:26]([CH2:29][CH2:30][C@@:31]([CH3:46])([S:42]([CH3:45])(=[O:43])=[O:44])[C:32]([NH:34][OH:35])=[O:33])[C:25](=[O:47])[CH:24]=1

Participants

3

Reactant 2

HCID 178448468HCID 178448468, compoundHCID 178448469HCID 178448469, compound

Product 1

HCID 178448471HCID 178448471, compoundYield 62.6%

Procedure

The title (0.16 g, 62.6%) compound was prepared from (2R)-4-[4-(2-fluoro-4-{[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methoxy}phenyl)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (0.35 g, 0.516 mmol) by a procedure analogous to that described for (2R)—N-hydroxy-4-[4-{4-[(cis-4-hydroxycyclohexyl)methoxy]phenyl}-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanamide, Example 8, Step F. LCMS m/z 511.7 (M+1) 1H NMR (400 MHz, DMSO-d6) δ ppm 0.94-1.25 (m, 4H) 1.57 (s, 3H) 1.60-1.75 (m, 1H) 1.83 (br. s., 4H) 2.08-2.24 (m, 1H) 2.35-2.48 (m, 1H) 3.11 (s, 3H) 3.28-3.44 (m, 1H) 3.65-3.80 (m, 1H) 3.84 (d, J=6.64 Hz, 2H) 4.01-4.22 (m, 1H) 6.47 (dt, J=7.18, 1.88 Hz, 1H) 6.53 (s, 1H) 6.87 (dd, J=8.79, 2.54 Hz, 1H) 6.94 (dd, J=13.38, 2.44 Hz, 1H) 7.51 (t, J=8.98 Hz, 1H) 7.71 (d, J=7.23 Hz, 1H) 9.24 (br. s., 1H) 11.15 (s, 1H)

Sources & evidence

ORD record
ord-1b831493b3064dae9bb1f0ace8987acd
Source dataset
uspto-grants-2014_03
Patent number
US08664401B2

Linked notes

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