HCID 67171388, compound → HCID 16041046, compound

HRID 545195Notes

Reaction equation

HRID 545195 reaction equation
C([O:8][C:9](=[O:45])[C:10]([C:13]1[CH:14]=[C:15]2[C:41](=[CH:42][CH:43]=1)[O:40][C:18]1([CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:35]=[C:34]([O:36][CH3:37])[C:33]4[C:28](=[C:29]([O:38][CH3:39])[CH:30]=[CH:31][CH:32]=4)[N:27]=3)=[O:25])[CH2:20][CH2:19]1)[CH2:17][C:16]2=[O:44])([CH3:12])[CH3:11])C1C=CC=CC=1>CO.[Pd]>[CH3:37][O:36][C:34]1[C:33]2[C:28](=[C:29]([O:38][CH3:39])[CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([C:24]([N:21]2[CH2:22][CH2:23][C:18]3([CH2:17][C:16](=[O:44])[C:15]4[C:41](=[CH:42][CH:43]=[C:13]([C:10]([CH3:12])([CH3:11])[C:9]([OH:45])=[O:8])[CH:14]=4)[O:40]3)[CH2:19][CH2:20]2)=[O:25])[CH:35]=1

Participants

4

Reactant 1

HCID 67171388HCID 67171388, compound

Product 1

HCID 16041046HCID 16041046, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-{1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]-4-oxospiro[chromane-2,4′-piperidin]-6-yl}-2-methylpropanoic acid benzyl ester (830 mg) was dissolved in 25 mL of MeOH and hydrogenated at 1.5 atmosphere over 100 mg of 10% Pd/C for 5 hrs. The mixture was filtered and the filtrate was concentrated and purified on preparative SiO2 PTC (CHCl3/MeOH=10:1) to give the intended compound as a colorless amorphous solid. 1H-NMR (400 MHz, CD3OD), 7.93 (1H, s), 7.88 (1H, d, J=2.3 Hz), 7.81 (1H, d, J=8.8 Hz), 7.65 (1H, dd, J=8.8 Hz, 2.3 Hz), 7.55 (1H, t, J=8.2 Hz), 7.27 (1H, J=8.2 Hz), 7.17 (1H, s), 7.10 (1H, d, J=8.2 Hz), 4.5-4.6 (1H, m), 4.15 (3H, s), 4.06 (3H, s), 3.3-3.7 (3H, m), 2.90 (1H, d, J=16.5 Hz), 2.84 (1H, d, J=16.5 Hz), 1.9-2.3 (4H, m). MS [M+H]+=519.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified on preparative SiO2 PTC (CHCl3/MeOH=10:1)

Sources & evidence

ORD record
ord-a96b6bfce13a4c1ab7219f87e64bd5e2
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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