HCID 86610170, compound → HCID 16041579, compound

HRID 2218276Notes

Reaction equation

HRID 2218276 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]([C:15]([N:17]2[CH2:22][CH2:21][C:20]3([CH2:31][C:30](=[O:32])[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([NH:33]C(=O)OCC5C=CC=CC=5)[CH:28]=4)[O:23]3)[CH2:19][CH2:18]2)=[O:16])[CH:4]=1>C1COCC1.CO.[Pd]>[NH2:33][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[O:23][C:20]1([CH2:21][CH2:22][N:17]([C:15]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:12]4[C:7](=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][CH:11]=4)[N:6]=3)=[O:16])[CH2:18][CH2:19]1)[CH2:31][C:30]2=[O:32]

Participants

5

Reactant 1

HCID 86610170HCID 86610170, compound

Product 1

HCID 16041579HCID 16041579, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.78 g of benzyl {1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4′-piperidin]-6-yl}carbamate was dissolved in 20 mL of THF and 40 mL of MeOH, and hydrogenated on 10% Pd/C at room temperature. Pd/C was removed through filtration, and the filtrate was concentrated to obtain the intended compound. 1H-NMR (CDCl3) δ: 7.77 (1H, dd, J=8.5, 1.2 Hz), 7.47 (1H, t, J=8.0 Hz), 7.17 (1H, s), 7.15 (1H, d, J=2.9 Hz), 7.08 (1H, dd, J=7.8, 1.0 Hz), 6.91 (1H, dd, J=8.8, 2.9 Hz), 6.85 (1H, d, J=8.8 Hz), 4.56 (1H, d, J=13.2 Hz), 4.16-4.08 (1H, m), 4.08 (3H, s), 4.03 (3H, s), 3.63-3.53 (3H, m), 3.34 (1H, td, J=12.8, 3.3 Hz), 2.76 (1H, d, J=16.5 Hz), 2.70 (1H, d, J=16.5 Hz), 2.20 (1H, dd, J=13.9, 2.7 Hz), 2.05 (1H, dd, J=13.9, 2.7 Hz), 1.88-1.78 (2H, m). MS [M+H]+=448.

Workup

  1. customat room temperature
  2. customPd/C was removed through filtration
  3. concentrationthe filtrate was concentrated
  4. customto obtain the intended compound

Sources & evidence

ORD record
ord-c166d648b528402bab0a00d64f234f36
Source dataset
uspto-grants-2008_08
Patent number
US07410976B2

Reaction notes

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