Tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate → Isopropyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)azepane-1-carboxylate

HRID 1895685Notes

Reaction equation

HRID 1895685 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28](C)([CH3:30])[CH3:29])=[O:26])[CH2:20][CH2:19]3)=[CH:13][C:12]2=[O:32])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CS(C1C=CC(N2C=CC(OC3CCN(C(OC(C)(C)C)=O)CC3)=CC2=O)=CC=1)(=O)=O>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]3[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][CH:28]([CH3:29])[CH3:30])=[O:26])[CH2:20][CH2:19]3)=[CH:13][C:12]2=[O:32])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 25204174Tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylateHCID 25204243HCID 25204243, compound

Product 1

HCID 25204244Isopropyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)azepane-1-carboxylate

Procedure

Example 7 was prepared according to procedures described in Example 3 substituting tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)azepane-1-carboxylate for tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate. 1H NMR (500 MHz, CDCl3) δ 8.08 (d, J=8.80 Hz, 2 H), 7.61 (d, J=8.80 Hz, 2 H), 7.29 (d, J=7.70 Hz, 1 H), 6.22 (s, 1 H), 6.17 (d, J=7.70 Hz, 1 H), 4.90-5.02 (m, 1 H), 4.48-4.56 (m, 1 H), 3.36-3.63 (m, 4 H), 3.11 (s, 3 H), 1.91-2.17 (m, 5 H), 1.64-1.77 (m, 1 H), 1.27 (d, J=6.05 Hz, 6 H). MS (ESI) 449 (M+H).

Workup

  1. customExample 7 was prepared

Sources & evidence

ORD record
ord-226b606cc9754fa3a4a0576d72efd248
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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