HCID 178448467, compound → HCID 178448470, compound

HRID 709216

Reaction equation

[CH3:1][C@@:2]([S:43]([CH3:46])(=[O:45])=[O:44])([CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([O:35]C4CCCCO4)[CH2:31][CH2:30]3)=[CH:23][CH:22]=2)=[CH:17][C:16]1=[O:42])[C:3]([NH:5][O:6]C1CCCCO1)=[O:4].ONC(=O)[C@](C)(S(C)(=O)=O)CCN1C=CC(C2C=CC(OC[C@H]3CC[C@@H](O)CC3)=CC=2)=CC1=O>>[OH:6][NH:5][C:3](=[O:4])[C@:2]([CH3:1])([S:43]([CH3:46])(=[O:45])=[O:44])[CH2:13][CH2:14][N:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@H:29]3[CH2:30][CH2:31][C@H:32]([OH:35])[CH2:33][CH2:34]3)=[CH:23][CH:22]=2)=[CH:17][C:16]1=[O:42]

Participants

Reactant 2

HCID 178448467HCID 178448467, compound

HCID 178448469HCID 178448469, compound

Product 1

HCID 178448470HCID 178448470, compoundYield 83.9%

Procedure

The title compound (300 mg, 83%) was prepared from (2R)-2-methyl-2-(methylsulfonyl)-4-[2-oxo-4-(4-{[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methoxy}phenyl)pyridin-1 (2H)-yl]-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (480 mg, 0.726 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 493.7 (M+1)1H NMR (400 MHz, DMSO-d6) δ ppm 0.92-1.23 (m, 4H) 1.54 (s, 3H) 1.58-1.72 (m, 1H) 1.81 (br. s., 4H) 2.06-2.21 (m, 1H) 2.41 (s, 1H) 3.08 (s, 3H) 3.25-3.41 (m, 1H) 3.74 (br. s., 1H) 3.80 (d, J=6.44 Hz, 2H) 3.98-4.17 (m, 1H) 6.48-6.71 (m, 2H) 6.85-7.06 (m, 2H) 7.52-7.78 (m, 3H) 11.15 (s, 1H)

Sources & evidence

ORD record: ord-d5de058df6394183aa2afd11c47c7103
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09180123B2

Linked notes

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